Organic compound, light-emitting device, thin film, light-emitting apparatus, electronic device, and lighting device

ABSTRACT

An organic compound with a long lifetime and high emission efficiency is provided. An organic compound represented by General Formula (G1) is provided. In the formula, any one of X 1  to X 4  represents N, another one represents C, and the others represent C or N. Any one of C is bonded to a group represented by General Formula (r1), and the others are bonded to hydrogen (H), an alkyl (R) group, a cycloalkyl (Cy) group, an aryl (Ar) group, or a heteroaryl (Het) group. Ar 1  represents an aromatic hydrocarbon, and is fused to an adjacent ring at a given site. When Ar 1  represents a benzene ring, the benzene ring includes an Ar group or a Het group. Q and Z represent O or S. Any of R 31  to R 34  represents a bond to any one of X 1  to X 4 , and the others represent H, an R group, a Cy group, an Ar group, or a Het group. Any one of R 35  to R 38  represents a polycyclic ring aromatic hydrocarbon group or a Het group, and the others represent H, an R group, a Cy group, an Ar group, or a Het group.

BACKGROUND OF THE INVENTION 1. Field of the Invention

One embodiment of the present invention relates to an organic compound, a light-emitting device, a light-emitting apparatus, a light-emitting and light-receiving apparatus, a display device, an electronic device, a lighting device, an organic device, and an electronic device. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the present invention disclosed in this specification and the like relates to an object, a method, or a manufacturing method. One embodiment of the present invention relates to a process, a machine, manufacture, or a composition of matter. Specifically, examples of the technical field of one embodiment of the present invention disclosed in this specification include a semiconductor device, a display device, a liquid-crystal device, a light-emitting apparatus, a lighting device, a power storage device, a memory device, an imaging device, a driving method thereof, and a manufacturing method thereof.

2. Description of the Related Art

Light-emitting devices (also referred to as organic EL elements or light-emitting elements) including organic compounds and utilizing electroluminescence (EL) have been put to more practical use. In the basic structure of such light-emitting devices, an organic compound layer containing a light-emitting material (an EL layer) is located between a pair of electrodes. Carriers are injected by application of voltage to the device, and recombination energy of the carriers is used, whereby light emission can be obtained from the light-emitting material.

Since such light-emitting devices are of self-emission type, the light-emitting elements are preferably used for pixels of a display with higher visibility than a liquid crystal display. Displays including such light-emitting devices are also highly advantageous in that they can be thin and lightweight because a backlight is not needed. Moreover, such light-emitting devices also have a feature that response speed is extremely fast.

Since light-emitting layers of such light-emitting devices can be successively formed two-dimensionally, planar light emission can be achieved. This feature is difficult to realize with point light sources typified by incandescent lamps or LEDs or linear light sources typified by fluorescent lamps; thus, such light-emitting devices also have great potential as planar light sources, which can be applied to lighting devices and the like.

Displays or lighting devices including light-emitting devices can be suitably used for a variety of electronic devices as described above, and research and development of light-emitting devices has progressed for higher efficiency or longer lifetimes.

Although the characteristics of light-emitting devices have been improved considerably, advanced requirements for various characteristics including efficiency and durability are not yet satisfied. In particular, to solve a problem such as burn-in that still remains as an issue peculiar to EL, it is preferable to suppress a reduction in efficiency due to degradation as much as possible.

Degradation largely depends on an emission center substance and its surrounding materials; therefore, host materials having good characteristics have been actively developed.

As host materials, organic compounds having indolocarbazole skeletons are disclosed, for example (Patent Documents 1 and 2). Organic compounds having indolocarbazole skeletons, which have high glass transition temperature, can offer favorable characteristics when used in light-emitting devices. Meanwhile, materials are being required to have higher heat resistance and a longer lifetime so that degradation of light-emitting devices can be reduced.

REFERENCE

-   [Patent Document 1] PCT International Publication No. WO2018/198844 -   [Patent Document 2] PCT International Publication No. WO2018/123783

SUMMARY OF THE INVENTION

An object of one embodiment of the present invention is to provide a novel organic compound. Another object is to provide an organic compound having a long lifetime. Another object is to provide an organic compound having high heat resistance. Another object is to provide an organic compound that can be used as a host material. Another object is to provide a light-emitting device having a long lifetime. Another object is to provide a light-emitting device having high emission efficiency. Another object is to provide a novel light-emitting device. Another object is to provide a light-emitting apparatus, an electronic device, or a lighting device having low power consumption.

Note that the description of these objects does not preclude the existence of other objects. In one embodiment of the present invention, there is no need to achieve all the objects. Other objects will be apparent from and can be derived from the descriptions of the specification, the drawings, the claims, and the like.

One embodiment of the present invention is an organic compound represented by General Formula (G1).

In General Formula (G1) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r1). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents any one of a substituted or unsubstituted polycyclic aromatic hydrocarbon group having 10 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.

One embodiment of the present invention is an organic compound represented by General Formula (G1′).

In General Formula (G1′) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r1). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Any one of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, another one of R³¹ to R³⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.

One embodiment of the present invention is an organic compound represented by General Formula (G2).

In General Formula (G2) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r2). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Any one of R³² to R³⁸ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³² to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a bond in General Formula (G2).

One embodiment of the present invention is an organic compound represented by General Formula (G3).

In General Formula (G3) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms forming a skeleton. Any of the substituents bonded to the carbon atom includes at least a dibenzofuran ring or a dibenzothiophene ring, and a carbazole ring. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Q represents an oxygen atom or a sulfur atom.

One embodiment of the present invention is an organic compound represented by General Formula (G2′).

In General Formula (G2′) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r2). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a substituted or unsubstituted group including a carbazole ring, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a bond in General Formula (G2′).

One embodiment of the present invention is an organic compound represented by General Formula (G4).

In General Formula (G4) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r3). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a bond to a, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group. In addition, * represents a bond in General Formula (G4).

Another embodiment of the present invention is an organic compound represented by General Formula (G5).

In General Formula (G5) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the others is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a bond, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group.

Another embodiment of the present invention is an organic compound represented by General Formula (G6).

In General Formula (G6) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ and R⁴³ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group.

Another embodiment of the present invention is an organic compound with any one of the above-described structures in which Ar¹ is represented by any one of General Formulae (t1), (t2-1), (t2-2), (t3-1) to (t3-3), and (t4).

In General Formulae (t1), (t2-1), (t2-2), (t3-1) to (t3-3), and (t4) above, any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R⁶ to R²⁷ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a site of fusion to a ring adjacent to Ar¹.

Another embodiment of the present invention is an organic compound represented by General Formula (G7).

In General Formula (G7) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, Ar² represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R¹, R², and R⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ and R⁴³ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group.

One embodiment of the present invention is an organic compound represented by General Formula (G8).

In General Formula (G8) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the others is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Furthermore, k represents an integer of 0 or 1. Each of R⁴¹, R⁴³ to R⁴⁸, and R⁵⁰ to R⁶⁶ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group.

Another embodiment of the present invention is an organic compound with any one of the above-described structures in which X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom.

Another embodiment of the present invention is an organic compound represented by any one of Structural Formulae (100) to (103).

Another embodiment of the present invention is a thin film including the organic compound having any of the above structures.

Another embodiment of the present invention is a light-emitting device including the organic compound having any of the above structures.

Another embodiment of the present invention is a light-emitting apparatus including the light-emitting device having the above structure, and at least one of a transistor and a substrate.

Another embodiment of the present invention is an electronic device including the above light-emitting apparatus; and a sensor unit, an input unit, or a communication unit.

Another embodiment of the present invention is a lighting device including the above light-emitting apparatus and a housing.

Note that the light-emitting device includes a device in which a layer including the organic compound with any of the above structures is interposed between a pair of electrodes, a device in which a layer including the organic compound is provided over a substrate, and the like. The light-emitting device also includes a layer (e.g., a cap layer, a partition wall, or a color filter) around an electrode or a substrate.

One embodiment of the present invention can provide a novel organic compound. Another embodiment of the present invention can provide an organic compound having a long lifetime. Another embodiment of the present invention can provide an organic compound having high heat resistance. Another embodiment of the present invention can provide an organic compound that can be used as a host material. Another embodiment of the present invention can provide an organic compound having an electron-transport property. Another embodiment of the present invention can provide a compound having a hole-transport property. Another embodiment of the present invention can provide a bipolar organic compound that transports both holes and electrons. Another embodiment of the present invention can provide a novel light-emitting device. Another embodiment of the present invention can provide a light-emitting device having excellent carrier balance and stability. Another embodiment of the present invention can provide a light-emitting device having a long lifetime. Another embodiment of the present invention can provide a light-emitting device having high emission efficiency. Another embodiment of the present invention can provide a light-emitting apparatus, an electronic device, or a lighting device having low power consumption.

Note that the description of these effects does not preclude the existence of other effects. One embodiment of the present invention does not necessarily have all the effects. Other effects will be apparent from and can be derived from the descriptions of the specification, the drawings, the claims, and the like.

BRIEF DESCRIPTION OF THE DRAWINGS

In the accompanying drawings:

FIGS. 1A to 1E illustrate structures of light-emitting devices according to an embodiment;

FIGS. 2A to 2D illustrate a light-emitting apparatus according to an embodiment;

FIGS. 3A to 3C illustrate a fabrication method of a light-emitting apparatus according to an embodiment;

FIGS. 4A to 4C illustrate a fabrication method of a light-emitting apparatus according to an embodiment;

FIGS. 5A to 5C illustrate a fabrication method of a light-emitting apparatus according to an embodiment;

FIGS. 6A to 6D illustrate a fabrication method of a light-emitting apparatus according to an embodiment;

FIGS. 7A to 7E illustrate a light-emitting apparatus according to an embodiment;

FIGS. 8A to 8F illustrate an apparatus and pixel arrangements according to an embodiment;

FIGS. 9A to 9C illustrate pixel circuits according to an embodiment;

FIG. 10 illustrates a light-emitting apparatus according to an embodiment;

FIGS. 11A to 11E illustrate electronic devices according to an embodiment;

FIGS. 12A to 12E illustrate electronic devices according to an embodiment;

FIGS. 13A and 13B illustrate electronic devices according to an embodiment;

FIGS. 14A and 14B illustrate a lighting device according to an embodiment;

FIG. 15 illustrates lighting devices according to an embodiment;

FIGS. 16A to 16C each illustrate a light-emitting device and a light-receiving device according to an embodiment;

FIGS. 17A and 17B each illustrate a light-emitting device and a light-receiving device according to an embodiment;

FIGS. 18A and 18B show a ¹H-NMR spectrum of 8BP-4 PCDBfBfpm;

FIG. 19 shows an absorption spectrum and an emission spectrum of a dichloromethane solution of 8BP-4PCDBfBfpm;

FIG. 20 shows an absorption spectrum and an emission spectrum of a thin film of 8BP-4PCDBfBfpm;

FIGS. 21A and 21B show a ¹H-NMR spectrum of 8BP-4mPCPDBfBfpm;

FIG. 22 shows an absorption spectrum and an emission spectrum of a dichloromethane solution of 8BP-4mPCPDBfBfpm;

FIG. 23 shows an absorption spectrum and an emission spectrum of a thin film of 8BP-4mPCPDBfBfpm;

FIGS. 24A and 24B show a ¹H-NMR spectrum of 8mpTP-4PCDBfBfpm;

FIG. 25 shows an absorption spectrum and an emission spectrum of a dichloromethane solution of 8mpTP-4PCDBfBfpm;

FIG. 26 shows an absorption spectrum and an emission spectrum of a thin film of 8mpTP-4PCDBfBfpm;

FIGS. 27A and 27B show a ¹H-NMR spectrum of 8mpTP-4mPCPDBfBfpm;

FIG. 28 shows an absorption spectrum and an emission spectrum of a dichloromethane solution of 8mpTP-4mPCPDBfBfpm;

FIG. 29 shows an absorption spectrum and an emission spectrum of a thin film of 8mpTP-4mPCPDBfBfpm;

FIG. 30 illustrates a structure of a light-emitting device according to examples;

FIG. 31 shows luminance-current density characteristics of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 32 shows current efficiency-luminance characteristics of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 33 shows luminance-voltage characteristics of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 34 shows current-voltage characteristics of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 35 shows external quantum efficiency-luminance characteristics of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 36 shows emission spectra of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 37 shows a luminance change over driving time of Light-emitting device 1, Light-emitting device 2, and Comparative light-emitting device 3;

FIG. 38 shows luminance-current density characteristics of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 39 shows current efficiency-luminance characteristics of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 40 shows luminance-voltage characteristics of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 41 shows current-voltage characteristics of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 42 shows external quantum efficiency-luminance characteristics of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 43 shows emission spectra of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 44 shows a luminance change over driving time of Light-emitting device 4, Light-emitting device 5, and Comparative light-emitting device 6;

FIG. 45 shows luminance-current density characteristics of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10;

FIG. 46 shows current efficiency-luminance characteristics of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10;

FIG. 47 shows luminance-voltage characteristics of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10;

FIG. 48 shows current-voltage characteristics of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10;

FIG. 49 shows external quantum efficiency-luminance characteristics of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10;

FIG. 50 shows emission spectra of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10; and

FIG. 51 shows a luminance change over driving time of Light-emitting device 7, Light-emitting device 8, Comparative light-emitting device 9, and Comparative light-emitting device 10.

DETAILED DESCRIPTION OF THE INVENTION Embodiment 1

In this embodiment, an organic compound and a thin film according to an embodiment of the present invention will be described.

One embodiment of the present invention is an organic compound including a six-membered heteroaromatic ring having a nitrogen atom and a heteroaromatic ring having a furan ring or a thiophene ring in a molecular structure, in which the rings may form a fused ring. Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as, for example, a host material in a light-emitting layer of a light-emitting device, the light-emitting device can have high emission efficiency and a long lifetime.

One embodiment of the present invention is an organic compound represented by General Formula (G1).

In General Formula (G1) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r1). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents any one of a substituted or unsubstituted polycyclic aromatic hydrocarbon group having 10 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as, for example, a host material, a light-emitting device can have high emission efficiency and a long lifetime.

One embodiment of the present invention is an organic compound represented by General Formula (G1′).

In General Formula (G1′) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r1). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Any one of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, another one of R³¹ to R³⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.

The organic compound represented by General Formula (G1) and the organic compound represented by General Formula (G1′) are different from each other in the position and kind of the substituent in the group represented by General Formula (r1). Specifically, the organic compound represented by General Formula (G1) has a structure in which any one of R³⁵ to R³⁸ represents any one of a substituted or unsubstituted polycyclic aromatic hydrocarbon group having 10 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton; the organic compound represented by General Formula (G1′) has a structure in which any one of R³¹ to R³⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Despite such differences in the position and kind of the substituent, the organic compound represented by General Formula (G1′) can have the same effect as the organic compound represented by General Formula (G1).

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as, for example, a host material, a light-emitting device can have high emission efficiency and a long lifetime.

One embodiment of the present invention is an organic compound represented by General Formula (G2).

In General Formula (G2) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r2). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Any one of R³² to R³⁸ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³² to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a bond in General Formula (G2).

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film even when the molecular weight is low. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as, for example, a host material, a light-emitting device can have high emission efficiency and a long lifetime.

One embodiment of the present invention is an organic compound represented by General Formula (G3).

In General Formula (G3) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms forming a skeleton. Any of the substituents bonded to the carbon atom includes at least a dibenzofuran ring or a dibenzothiophene ring, and a carbazole ring. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Q represents an oxygen atom or a sulfur atom.

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as a host material, for example, a light-emitting device having high emission efficiency, a long lifetime, and low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided.

One embodiment of the present invention is an organic compound represented by General Formula (G2′).

In General Formula (G2′) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r2). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a substituted or unsubstituted group including a carbazole ring, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a bond in General Formula (G2′).

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. When the organic compound having such a structure is used as a host material, for example, a light-emitting device having high emission efficiency, a long lifetime, and low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided.

One embodiment of the present invention is an organic compound represented by General Formula (G4).

In General Formula (G4) above, any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom. Any one of the carbon atoms is bonded to a group represented by General Formula (r3). Each of the others of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a bond, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and an example of the aryl group is a phenyl group. In addition, * represents a bond in General Formula (G4).

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. The organic compound having such a structure is preferably used as, for example, a host material, in which case a light-emitting device can have high emission efficiency and a long lifetime. Furthermore, a light-emitting device having low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided.

Another embodiment of the present invention is an organic compound represented by General Formula (G5).

In General Formula (G5) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the others is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵ to R³⁸ represents a bond, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and an example of the aryl group is a phenyl group.

Such a structure enables the organic compound to have high heat resistance and stability and to form a very stable thin film. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. The organic compound having such a structure is preferably used as, for example, a host material, in which case a light-emitting device can have high emission efficiency and a long lifetime. Furthermore, a light-emitting device having low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided.

Another embodiment of the present invention is an organic compound represented by General Formula (G6).

In General Formula (G6) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site. When Ar¹ represents a benzene ring, the benzene ring includes at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, a represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ and R⁴³ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and an example of the aryl group is a phenyl group.

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. In addition, the structure is preferred because an evaporation film that is unlikely to deteriorate at evaporation and has stability can be formed. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. The organic compound having such a structure is preferably used as, for example, a host material, in which case a light-emitting device can have high emission efficiency and a long lifetime. Furthermore, a light-emitting device having low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided.

Another embodiment of the present invention is an organic compound with any one of the above-described structures in which Ar¹ is represented by any one of General Formulae (t1), (t2-1), (t2-2), (t3-1) to (t3-3), and (t4).

In General Formulae (t1), (t2-1), (t2-2), (t3-1) to (t3-3), and (t4) above, any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R⁶ to R²⁷ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, * represents a site of fusion to a ring adjacent to Ar¹.

As Ar¹, the structure represented by any of (t1), (t2-1), (t2-2), (t3-1) to (t3-3), and (t4) is used and fused to an adjacent ring, whereby the compound can have higher heat resistance and higher stability. The compound can have a molecular structure suitable for energy transfer to a light-emitting material when used as a host in a light-emitting layer. For the use as a host particularly in a phosphorescent light-emitting layer, when the emission spectrum of the host is made to overlap with an absorption edge of the light-emitting material, energy transfer from the host to the light-emitting material can occur with higher efficiency and accordingly higher emission efficiency, lower driving voltage, and a longer lifetime can be expected. Thus, the molecular design suitable for the light-emitting material is important. For the use as a host in a light-emitting layer in a green element, (t1), which enables the highest T₁ level, is suitably used. For the use as a host in a light-emitting layer in a red to near-infrared element, any of (t2) to (t4) is suitably used. Modification of the thus fused ring structure can change the band gap and make the T₁ and S₁ levels appropriate, for example.

Another embodiment of the present invention is an organic compound represented by General Formula (G7).

In General Formula (G7) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. In addition, Ar² represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R¹, R², and R⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Each of R⁴¹ and R⁴³ to R⁴⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and an example of the aryl group is a phenyl group.

Such a structure enables the organic compound to have high heat resistance and stability and to form a stable thin film. In addition, the structure is preferred because an evaporation film that is unlikely to deteriorate at evaporation and has stability can be formed. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. The organic compound having such a structure is preferably used as, for example, a host material, in which case a light-emitting device can have high emission efficiency and a long lifetime. Furthermore, a light-emitting device having low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided. For the use as a host in a phosphorescent light-emitting layer, in particular, such a structure enables the organic compound to be suitably used as a host in a light-emitting layer of a green element or a host in a light-emitting layer that emits light with a wavelength longer than the wavelength of green light.

One embodiment of the present invention is an organic compound represented by General Formula (G8).

In General Formula (G8) above, each of X² to X⁴ independently represents a carbon atom or a nitrogen atom. Each of the carbon atoms is independently bonded to any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, each of Q and Z independently represents an oxygen atom or a sulfur atom. Each of R³² to R³⁴ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Any one of R³⁵, R³⁶ and R³⁸ represents a substituted or unsubstituted group including a carbazole ring, and each of the others of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3. Furthermore, k represents an integer of 0 or 1. Each of R⁴¹, R⁴³ to R⁴⁸, and R⁵⁰ to R⁶⁶ independently represents any one of hydrogen (including deuterium), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton. Furthermore, R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and an example of the aryl group is a phenyl group.

The structure represented by any of General Formulae (G1) to (G8) enables the organic compound to have high heat resistance and stability and to form a stable thin film. In addition, the structure is preferred because an evaporation film that is unlikely to deteriorate at evaporation and has stability can be formed. Furthermore, the organic compound is electrically resistant to oxidation and reduction and thus can be favorably used in a light-emitting device. Moreover, owing to the molecular structure where electrons and holes can be transferred, the organic compound can provide a good carrier balance when used in a light-emitting device. The organic compound can also have a high carrier-transport property. The organic compound having such a structure is preferably used as, for example, a host material, in which case a light-emitting device can have high emission efficiency and a long lifetime. Furthermore, a light-emitting device having low driving voltage can be provided and accordingly a light-emitting apparatus, an electronic device, or a lighting device having low power consumption can be provided. For the use as a host in a phosphorescent light-emitting layer, in particular, such a structure enables the organic compound to be suitably used as a host in a light-emitting layer of a green element or a host in a light-emitting layer that emits light with a wavelength longer than the wavelength of green light.

Another embodiment of the present invention is an organic compound with any of the above structures in which X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom. Such a structure can improve the carrier-transport property.

Specific examples of the alkyl group having 1 to 10 carbon atom in General Formulae (G1) to (G8) above include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, and a 2,3-dimethylbutyl group. In the case where an alkyl group having 1 to 6 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms forming a skeleton, and a heteroaryl group having 2 to 30 carbon atoms forming a skeleton.

In General Formulae (G1) to (G8), specific examples of the cycloalkyl group having 3 to 10 carbon atoms that can be used include a cyclopropyl group, a methylisopropyl group, a cyclobutyl group, a methylcyclobutyl group, a cyclopentyl group, a methylcyclopentyl group, an isopropylcyclopentyl group, a tert-butylcyclopropyl group, a cyclohexyl group, a methylcyclohexyl group, an isopropylcyclohexyl group, a tert-butylcyclohexyl group, a cyclopentyl group, a methylcycloheptyl group, an isopropylcycloheptyl group, a cyclooctyl group, a methylcyclooctyl group, a cyclononyl group, a methylcyclononyl group, and a cyclodecyl group. In the case where a cycloalkyl group having 3 to 10 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms forming a skeleton, and a heteroaryl group having 2 to 30 carbon atoms forming a skeleton.

In General Formulae (G1) to (G8), the number of carbon atoms of the aryl group or the heteroaryl group which form a skeleton is not limited to the above. For example, increasing the number of carbon atoms of the aryl group or the heteroaryl group which form a skeleton can improve the heat resistance. However, increasing the number of carbon atoms of the aryl group or the heteroaryl group which form a skeleton might impair the sublimation property; the number of the carbon atoms is 60 or less, preferably 30 or less, further preferably 21 or less, and still further preferably 18 or less. Specifically, an aryl group having 6 to 60 carbon atoms forming a skeleton or a heteroaryl group having 2 to 60 carbon atoms forming a skeleton can be used in General Formulae (G1) to (G8), for example. The aryl group having 6 to 30 carbon atoms forming a skeleton and the heteroaryl group having 2 to 60 carbon atoms forming a skeleton are preferably represented by any of (Ar-1) to (Ar-107).

Note that the substituents represented by Structural Formulae (Ar-1) to (Ar-109) are examples of the aryl group having 6 to 30 carbon atoms forming a skeleton and the heteroaryl group having 2 to 30 carbon atoms forming a skeleton; however, the aryl group having 6 to 30 carbon atoms forming a skeleton and the heteroaryl group having 2 to 30 carbon atoms forming a skeleton that can be used in General Formulae (G1) to (G8) are not limited to the substituents represented by General Formulae (Ar-1) to (Ar-109).

In General Formulae (G1) to (G8) above, when the aryl group and the heteroaryl group (including a carbazolyl group) has a substituent, the substituent is an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms forming a skeleton, or a heteroaryl group having 2 to 30 carbon atoms forming a skeleton.

In General Formulae (G4) to (G7) above, specific examples of the arylene group having 6 to 13 carbon atoms forming a skeleton include a phenylene group, a naphthalenediyl group, a biphenyldiyl group, and a fluorene diyl group. Note that the arylene group having 6 to 13 carbon atoms forming a skeleton which can be used in General Formulae (G4) to (G7) is not limited to these examples. When an arylene group is used as a substituent, i.e., when n is greater than or equal to 1 and less than or equal to 3 in General Formulae (G4) to (G7), the highest occupied molecular orbital (HOMO) level can be changed to adjust the carrier balance or to improve the heat resistance. In the case where an arylene group having 6 to 13 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms forming a skeleton, and a heteroaryl group having 2 to 30 carbon atoms forming a skeleton. When an alkyl group is included as a substituent, the refractive index can be low. When an aryl group or a heteroaryl group is included, the heat resistance can be improved.

Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, and a 2,3-dimethylbutyl group. Specific examples of the aryl group having 6 to 13 carbon atoms forming a skeleton include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a biphenyl group, a naphthyl group, and a fluorenyl group.

For use in a light-emitting device, the organic compound of one embodiment of the present invention represented by any of General Formulae (G1) to (G8) above is preferably formed into a thin film (also referred to as an organic compound layer). A thin film including the organic compound of one embodiment of the present invention can be suitably used for a light-emitting layer, a hole-transport layer, an electron-transport layer, or a cap layer in a light-emitting device. In addition, the organic compound of one embodiment of the present invention can be used also for a non-light-emitting device. As the non-light-emitting device, a device such as a light-receiving device can be given, for example. Note that a light-emitting device and a light-receiving device are collectively referred to as an organic device in some cases.

Note that the structure in the case of using the organic compound of one embodiment of the present invention for a light-emitting layer, a hole-transport layer, an electron-transport layer, or a cap layer in a light-emitting device, or in the case of using the organic compound of one embodiment of the present invention for a light-receiving device is described in detail in Embodiment 2.

The following are specific examples of the organic compounds of one embodiment of the present invention each having any one of the above structures represented by General Formulae (G1) to (G8) above.

The organic compounds represented by Structural Formulae (100) to (163) and (200) to (237) above are examples of the organic compounds represented by General Formulae (G1) to (G8); however, the organic compound of one embodiment of the present invention is not limited to the examples.

<<Method of Synthesizing Compound Represented by General Formula (G5)>>

Next, as an example of a method of synthesizing the organic compound of one embodiment of the present invention, a method of synthesizing the organic compound represented by General Formula (G5) is described. A variety of reactions can be applied to a method for synthesizing the organic compound of one embodiment of the present invention. Thus, the method for synthesizing the organic compound of one embodiment of the present invention is not limited to the synthesis methods below.

In General Formula (G5), any of the above-described elements or substituents can be used as X² to X⁴, R³² to R³⁸, R⁴¹ to R⁴⁹, a, Q, Z and Ar¹. Moreover, n represents an integer greater than or equal to 0 and less than or equal to 3.

The organic compound represented by General Formula (G5) can be synthesized as in Synthesis Schemes (a-1) and (a-2) shown below.

In Synthesis Schemes (a-1) and (a-2), each of B¹ to B⁵ may independently be chlorine, bromine, iodine, a triflate group, an organoboron group, boronic acid, organoaluminum, organozirconium, organozinc, an organotin group, or the like.

In Compound 1, B¹ is bonded to or substituted by any one of R³⁵ to R³⁸. In Compound 2, B³ is bonded to or substituted by any one of R⁴¹ to R⁴⁴ via (α)_(n).

The coupling reaction as in Synthesis schemes (a-1) and (a-2) can produce the compound represented by General Formula (G5). In Synthesis Scheme (a-1), for example, when B¹, B², and B³ are bromine, chlorine, and boronic acid, respectively, (α)_(n) can be bonded to the site of B¹ in Compound 1 because the coupling reaction proceeds more easily at bromine than at chlorine.

Synthesis schemes (a-1) and (a-2) can be performed by the Suzuki-Miyaura coupling reaction, for example. Examples of the palladium catalyst for that case include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), and bis(triphenylphosphine)palladium(II)dichloride. Examples of a ligand of the palladium catalyst include tri(ortho-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.

Examples of the base that can be used in the reactions in Synthesis schemes (a-1) and (a-2) include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, sodium carbonate, potassium phosphate, and potassium acetate.

Examples of the solvent that can be used in the reactions in Synthesis schemes (a-1) and (a-2) include a mixed solvent of toluene and water; a mixed solvent of toluene, an alcohol such as ethanol, and water; a mixed solvent of xylene and water; a mixed solvent of xylene, an alcohol such as ethanol, and water; a mixed solvent of benzene and water; a mixed solvent of benzene, an alcohol such as ethanol, and water; and a mixed solvent of water and an ether such as diethylene glycol dimethyl ether. Note that a mixed solvent of toluene and water; a mixed solvent of toluene, ethanol, and water; or a mixed solvent of an ether such as diethylene glycol dimethyl ether and water is further preferable.

Note that any palladium catalyst, ligand, base, and solvent other than the above examples may be used.

In Synthesis Schemes (a-1) and (a-2), any of R³¹ to R³⁸ may be deuterium. The substituent at any of R³¹ to R³⁸, X¹ to X⁴, and Ar¹ may be deuterium. In such a case, a compound obtained by deuteration of Compound 1 or Compound 2 is used for the coupling reaction. Examples of the solvent that can be used in a reaction performing deuteration include benzene-d6, toluene-d8, xylene-d10, and heavy water. Examples of the catalyst that can be used include molybdenum(V) chloride, tungsten(VI) chloride, niobium(V) chloride, tantalum(V) chloride, aluminum(III) chloride, titanium(IV) chloride, and tin(IV) chloride. However, the solvent and the catalyst are not limited to these examples.

The organic compounds represented by other general formulae (General Formula (G1) to (G4) and (G6) to (G8)) can also be synthesized as described above.

The structures described in this embodiment can be used in combination with any of the structures described in the other embodiments as appropriate.

Embodiment 2

In this embodiment, structures of the light-emitting devices including any of the organic compounds described in Embodiment 1 are described with reference to FIGS. 1A to 1E.

<<Basic Structure of Light-Emitting Device>>

A basic structure of a light-emitting device is described. FIG. 1A illustrates a light-emitting device including, between a pair of electrodes, an EL layer including a light-emitting layer. Specifically, the EL layer 103 is positioned between the first electrode 101 and the second electrode 102.

FIG. 1B illustrates a light-emitting device that has a stacked-layer structure (tandem structure) in which a plurality of EL layers (two EL layers 103 a and 103 b in FIG. 1B) are provided between a pair of electrodes and a charge-generation layer 106 is provided between the EL layers. A light-emitting device having a tandem structure enables fabrication of a light-emitting apparatus that has high efficiency without changing the amount of current.

The charge-generation layer 106 has a function of injecting electrons into one of the EL layers 103 a and 103 b and injecting holes into the other of the EL layers 103 a and 103 b when a potential difference is caused between the first electrode 101 and the second electrode 102. Thus, when voltage is applied in FIG. 1B such that the potential of the first electrode 101 can be higher than that of the second electrode 102, electrons are injected into the EL layer 103 a from the charge-generation layer 106 and holes are injected into the EL layer 103 b from the charge-generation layer 106.

Note that in terms of light extraction efficiency, the charge-generation layer 106 preferably has a property of transmitting visible light (specifically, the charge-generation layer 106 preferably has a visible light transmittance of 40% or more). The charge-generation layer 106 functions even if it has lower conductivity than the first electrode 101 or the second electrode 102.

FIG. 1C illustrates a stacked-layer structure of the EL layer 103 in the light-emitting device of one embodiment of the present invention. In this case, the first electrode 101 is regarded as functioning as an anode and the second electrode 102 is regarded as functioning as a cathode. The EL layer 103 has a structure in which the hole-injection layer 111, the hole-transport layer 112, the light-emitting layer 113, the electron-transport layer 114, and the electron-injection layer 115 are stacked in this order over the first electrode 101. Note that the light-emitting layer 113 may have a stacked-layer structure of a plurality of light-emitting layers that emit light of different colors. For example, a light-emitting layer containing a light-emitting substance that emits red light, a light-emitting layer containing a light-emitting substance that emits green light, and a light-emitting layer containing a light-emitting substance that emits blue light may be stacked with or without a layer containing a carrier-transport material therebetween. Alternatively, a light-emitting layer containing a light-emitting substance that emits yellow light and a light-emitting layer containing a light-emitting substance that emits blue light may be used in combination. Note that the stacked-layer structure of the light-emitting layer 113 is not limited to the above. For example, the light-emitting layer 113 may have a stacked-layer structure of a plurality of light-emitting layers that emit light of the same color. For example, a first light-emitting layer containing a light-emitting substance that emits blue light and a second light-emitting layer containing a light-emitting substance that emits blue light may be stacked with or without a layer containing a carrier-transport material therebetween. The structure in which a plurality of light-emitting layers that emit light of the same color are stacked can achieve higher reliability than a single-layer structure in some cases. In the case where a plurality of EL layers are provided as in the tandem structure illustrated in FIG. 1B, the layers in each EL layer are sequentially stacked from the anode side as described above. When the first electrode 101 is the cathode and the second electrode 102 is the anode, the stacking order of the layers in the EL layer 103 is reversed. Specifically, the layer 111 over the first electrode 101 serving as the cathode is an electron-injection layer; the layer 112 is an electron-transport layer; the layer 113 is a light-emitting layer; the layer 114 is a hole-transport layer; and the layer 115 is a hole-injection layer.

The light-emitting layer 113 included in each of the EL layers (103, 103 a, and 103 b) contains an appropriate combination of a light-emitting substance and a plurality of substances, so that fluorescent light of a desired color or phosphorescent light of a desired color can be obtained. The light-emitting layer 113 may have a stacked-layer structure having different emission colors. In that case, light-emitting substances and other substances are different between the stacked light-emitting layers. Alternatively, the plurality of EL layers (103 a and 103 b) in FIG. 1B may exhibit their respective emission colors. Also in that case, the light-emitting substances and other substances are different between the stacked light-emitting layers.

The light-emitting device of one embodiment of the present invention can have a micro optical resonator (microcavity) structure when, for example, the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode in FIG. 1C. Thus, light from the light-emitting layer 113 in the EL layer 103 can be resonated between the electrodes and light emitted through the second electrode 102 can be intensified.

Note that when the first electrode 101 of the light-emitting device is a reflective electrode having a stacked-layer structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by adjusting the thickness of the transparent conductive film. Specifically, when the wavelength of light obtained from the light-emitting layer 113 is k, the optical path length between the first electrode 101 and the second electrode 102 (the product of the thickness and the refractive index) is preferably adjusted to be mk/2 (m is an integer of 1 or more) or close to mV/2.

To amplify desired light (wavelength: k) obtained from the light-emitting layer 113, it is preferable to adjust each of the optical path length from the first electrode 101 to a region where the desired light is obtained in the light-emitting layer 113 (light-emitting region) and the optical path length from the second electrode 102 to the region where the desired light is obtained in the light-emitting layer 113 (light-emitting region) to be (2m′+1)λ/4 (m′ is an integer of 1 or more) or close to (2m′+1)λ/4. Here, the light-emitting region means a region where holes and electrons are recombined in the light-emitting layer 113.

By such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

In the above case, the optical path length between the first electrode 101 and the second electrode 102 is, to be exact, the total thickness from a reflective region in the first electrode 101 to a reflective region in the second electrode 102. However, it is difficult to precisely determine the reflective regions in the first electrode 101 and the second electrode 102; thus, it is assumed that the above effect can be sufficiently obtained wherever the reflective regions may be set in the first electrode 101 and the second electrode 102. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is, to be exact, the optical path length between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that emits the desired light. However, it is difficult to precisely determine the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that emits the desired light; thus, it is assumed that the above effect can be sufficiently obtained wherever the reflective region and the light-emitting region may be set in the first electrode 101 and the light-emitting layer that emits the desired light, respectively.

The light-emitting device illustrated in FIG. 1D is a light-emitting device having a tandem structure. Owing to a microcavity structure, light (monochromatic light) with different wavelengths from the EL layers (103 a and 103 b) can be extracted. Thus, separate coloring for obtaining a plurality of emission colors (e.g., R, G, and B) is not necessary. Therefore, high resolution can be easily achieved. A combination with coloring layers (color filters) is also possible. Furthermore, the emission intensity of light with a specific wavelength in the front direction can be increased, whereby power consumption can be reduced.

The light-emitting device illustrated in FIG. 1E is an example of the light-emitting device having the tandem structure illustrated in FIG. 1B, and includes three EL layers (103 a, 103 b, and 103 c) stacked with charge-generation layers (106 a and 106 b) positioned therebetween, as illustrated in FIG. 1E. The three EL layers (103 a, 103 b, and 103 c) include respective light-emitting layers (113 a, 113 b, and 113 c), and the emission colors of the light-emitting layers can be selected freely. For example, the light-emitting layer 113 a can emit blue light, the light-emitting layer 113 b can emit red light, green light, or yellow light, and the light-emitting layer 113 c can emit blue light, or the light-emitting layer 113 a can emit red light, the light-emitting layer 113 b can emit blue light, green light, or yellow light, and the light-emitting layer 113 c can emit red light.

In the light-emitting device of one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (e.g., a transparent electrode or a transflective electrode). In the case where the light-transmitting electrode is a transparent electrode, the transparent electrode has a visible light transmittance higher than or equal to 40%. In the case where the light-transmitting electrode is a transflective electrode, the transflective electrode has a visible light reflectance higher than or equal to 20% and lower than or equal to 80%, preferably higher than or equal to 40% and lower than or equal to 70%. These electrodes preferably have a resistivity of 1×10⁻² Ωcm or less.

When one of the first electrode 101 and the second electrode 102 is a reflective electrode in the light-emitting device of one embodiment of the present invention, the visible light reflectance of the reflective electrode is higher than or equal to 40% and lower than or equal to 100%, preferably higher than or equal to 70% and lower than or equal to 100%. This electrode preferably has a resistivity of 1×10⁻² Ωcm or less.

<<Specific Structure of Light-Emitting Device>>

Next, a specific structure of the light-emitting device of one embodiment of the present invention will be described. Here, the description is made using FIG. 1D illustrating the tandem structure. Note that the structure of the EL layer applies also to the structure of the light-emitting devices having a single structure in FIGS. 1A and 1C. When the light-emitting device in FIG. 1D has a microcavity structure, the first electrode 101 is formed as a reflective electrode and the second electrode 102 is formed as a transflective electrode. Thus, a single-layer structure or a stacked-layer structure can be formed using one or more kinds of desired electrode materials. Note that the second electrode 102 is formed after formation of the EL layer 103 b, with the use of a material selected as appropriate.

<First Electrode and Second Electrode>

As materials for the first electrode 101 and the second electrode 102, any of the following materials can be used in an appropriate combination as long as the above functions of the electrodes can be fulfilled. For example, a metal, an alloy, an electrically conductive compound, a mixture of these, and the like can be used as appropriate. Specifically, an In—Sn oxide (also referred to as ITO), an In—Si—Sn oxide (also referred to as ITSO), an In—Zn oxide, or an In—W—Zn oxide can be used. In addition, it is possible to use a metal such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), or neodymium (Nd) or an alloy containing an appropriate combination of any of these metals. It is also possible to use a Group 1 element or a Group 2 element in the periodic table that is not described above (e.g., lithium (Li), cesium (Cs), calcium (Ca), or strontium (Sr)), a rare earth metal such as europium (Eu) or ytterbium (Yb), an alloy containing an appropriate combination of any of these elements, graphene, or the like.

In the light-emitting device in FIG. 1D, when the first electrode 101 is the anode, a hole-injection layer 111 a and a hole-transport layer 112 a of the EL layer 103 a are sequentially stacked over the first electrode 101 by a vacuum evaporation method. After the EL layer 103 a and the charge-generation layer 106 are formed, a hole-injection layer 111 b and a hole-transport layer 112 b of the EL layer 103 b are sequentially stacked over the charge-generation layer 106 in a similar manner.

<Hole-Injection Layer>

The hole-injection layers (111, 111 a, and 111 b) inject holes from the first electrode 101 serving as the anode and the charge-generation layers (106, 106 a, and 106 b) to the EL layers (103, 103 a, and 103 b) and contain an organic acceptor material or a material having a high hole-injection property.

The organic acceptor material allows holes to be generated in another organic compound whose HOMO level is close to the lowest unoccupied molecular orbital (LUMO) level of the organic acceptor material when charge separation is caused between the organic acceptor material and the organic compound. Thus, as the organic acceptor material, a compound having an electron-withdrawing group (e.g., a halogen group or a cyano group), such as a quinodimethane derivative, a chloranil derivative, and a hexaazatriphenylene derivative, can be used. Examples of the organic acceptor material include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F₄-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile. Note that among organic acceptor materials, a compound in which electron-withdrawing groups are bonded to fused aromatic rings each having a plurality of heteroatoms, such as HAT-CN, is particularly preferred because it has a high acceptor property and stable film quality against heat. Besides, a [3]radialene derivative having an electron-withdrawing group (particularly a cyano group or a halogen group such as a fluoro group), which has a very high electron-accepting property, is preferred; specific examples include α,α′,α″-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α′,α″-1,2,3-cyclopropanetriylidenetris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α′,α″-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile].

As the material having a high hole-injection property, an oxide of a metal belonging to Group 4 to Group 8 in the periodic table (e.g., a transition metal oxide such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, or manganese oxide) can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among these oxides, molybdenum oxide is preferable because it is stable in the air, has a low hygroscopic property, and is easily handled. Other examples are phthalocyanine (abbreviation: H₂Pc) and a phthalocyanine-based compound such as copper phthalocyanine (abbreviation: CuPc), and the like.

Other examples are aromatic amine compounds, which are low-molecular compounds, such as 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N′-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

Other examples are high-molecular compounds (e.g., oligomers, dendrimers, and polymers) such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Alternatively, it is possible to use a high-molecular compound to which acid is added, such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (abbreviation: PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (abbreviation: PAni/PSS), for example.

As the material having a high hole-injection property, a mixed material containing a hole-transport material and the above-described organic acceptor material (electron-accepting material) can be used. In that case, the organic acceptor material extracts electrons from the hole-transport material, so that holes are generated in the hole-injection layer 111 and the holes are injected into the light-emitting layer 113 through the hole-transport layer 112. Note that the hole-injection layer 111 may be formed to have a single-layer structure using a mixed material containing a hole-transport material and an organic acceptor material (electron-accepting material), or a stacked-layer structure of a layer containing a hole-transport material and a layer containing an organic acceptor material (electron-accepting material).

The hole-transport material preferably has a hole mobility higher than or equal to 1×10⁻⁶ cm²/Vs in the case where the square root of the electric field strength [V/cm] is 600. Note that other substances can also be used as long as the substances have hole-transport properties higher than electron-transport properties.

As the hole-transport material, materials having a high hole-transport property, such as a compound having a π-electron rich heteroaromatic ring (e.g., a carbazole derivative, a furan derivative, and a thiophene derivative) and an aromatic amine (an organic compound having an aromatic amine skeleton), are preferable. The compound in Embodiment 1 has a hole-transport property and thus can be used as a hole-transport material.

Examples of the carbazole derivative (an organic compound having a carbazole ring) include a bicarbazole derivative (e.g., a 3,3′-bicarbazole derivative) and an aromatic amine having a carbazolyl group.

Specific examples of the bicarbazole derivative (e.g., a 3,3′-bicarbazole derivative) include 3,3′-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9′-bis(biphenyl-4-yl)-3,3′-bi-9H-carbazole (abbreviation: BisBPCz), 9,9′-bis(1,1′-biphenyl-3-yl)-3,3′-bi-9H-carbazole (abbreviation: BismBPCz), 9-(1,1′-biphenyl-3-yl)-9′-(1,1′-biphenyl-4-yl)-9H,9′H-3,3′-bicarbazole (abbreviation: mBPCCBP), and 9-(2-naphthyl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (abbreviation: βNCCP).

Specific examples of the aromatic amine having a carbazolyl group include 4-phenyl-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-bis(9,9-dimethyl-9H-fluoren-2-yl)amine (abbreviation: PCBFF), N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-4-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-4-amine, N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-2-amine, N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-4-amine, N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9′-spirobi(9H-fluoren)-2-amine, N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9′-spirobi(9H-fluoren)-4-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[1,1′:3′,1″-terphenyl-4-yl]-9,9-dimethyl-9H-fluoren-2-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[1,1′:4′,1″-terphenyl-4-yl]-9,9-dimethyl-9H-fluoren-2-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[1,1′:3′,1″-terphenyl-4-yl]-9,9-dimethyl-9H-fluoren-4-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[1,1′:4′,1″-terphenyl-4-yl]-9,9-dimethyl-9H-fluoren-4-amine, 4,4′-diphenyl-4″-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4′-di(1-naphthyl)-4″-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N′-bis(9-phenylcarbazol-3-yl)-N,N′-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N′,N″-triphenyl-N,N′,N″-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9′-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N′-bis[4-(carbazol-9-yl)phenyl]-N,N′-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), and 4,4′,4″-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA).

Other examples of the carbazole derivative include 9-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]phenanthrene (abbreviation: PCPPn), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4′-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA).

Specific examples of the furan derivative (an organic compound having a furan ring) include 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

Specific examples of the thiophene derivative (an organic compound having a thiophene ring) include organic compounds having a thiophene ring, such as 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV).

Specific examples of the aromatic amine include 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3′-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N-phenyl-N-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9′-bifluorene (abbreviation: DPASF), 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9′-bifluorene (abbreviation: DPA2SF), 4,4′,4″-tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1′-TNATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N′-di(p-tolyl)-N,N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4′-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4″-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4′,4″-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4′,4″-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4′-diphenyl-4″-(6;1′-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4′-diphenyl-4″-(7;1′-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4′-diphenyl-4″-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4′-diphenyl-4″-(6;2′-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4′-diphenyl-4″-(7;2′-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4′-diphenyl-4″-(4;2′-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4′-diphenyl-4″-(5;2′-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4′-(2-naphthyl)-4″-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4′-[4-(2-naphthyl)phenyl]-4″-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4′-[4-(2-naphthyl)phenyl]-4″-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4′-(1-naphthyl)-triphenylamine (abbreviation: αNBA1BP), 4,4′-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4′-diphenyl-4″-[4′-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4′-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1′-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4′-(carbazol-9-yl)biphenyl-4-yl]-4′-(2-naphthyl)-4″-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9′-spirobi[9H-fluoren]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1′-biphenyl]-4-yl)-9,9′-spirobi[9H-fluoren]-2-amine (abbreviation: BBASF), N,N-bis([1,1′-biphenyl]-4-yl)-9,9′-spirobi[9H-fluoren]-4-amine (abbreviation: BBASF(4)), N-(1,1′-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi[9H-fluoren]-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4′-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-2-amine, and N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-1-amine.

Other examples of the hole-transport material include high-molecular compounds (e.g., oligomers, dendrimers, and polymers) such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-V-phenylamino}phenyl)methacrylamide](abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine](abbreviation: Poly-TPD). Alternatively, it is possible to use a high-molecular compound to which acid is added, such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (abbreviation: PEDOT/PSS) or polyaniline/poly(styrenesulfonic acid) (abbreviation: PAni/PSS), for example.

Note that the hole-transport material is not limited to the above examples, and any of a variety of known materials may be used alone or in combination as the hole-transport material.

The hole-injection layers (111, 111 a, and 111 b) can be formed by any of known film formation methods, and for example, a vacuum evaporation method can be employed.

<Hole-Transport Layer>

The hole-transport layers (112, 112 a, and 112 b) transport the holes, which are injected from the first electrodes 101 by the hole-injection layers (111, 111 a, and 111 b), to the light-emitting layers (113, 113 a, and 113 b). Note that the hole-transport layers (112, 112 a, and 112 b) each contain a hole-transport material. Thus, the hole-transport layers (112, 112 a, and 112 b) can be formed using hole-transport materials that can be used for the hole-injection layers (111, 111 a, and 111 b).

Note that in the light-emitting device of one embodiment of the present invention, the organic compound used for the hole-transport layers (112, 112 a, and 112 b) can also be used for the light-emitting layers (113, 113 a, 113 b, and 113 c). The use of the same organic compound for the hole-transport layers (112, 112 a, and 112 b) and the light-emitting layers (113, 113 a, 113 b, and 113 c) is preferable, in which case holes can be efficiently transported from the hole-transport layers (112, 112 a, and 112 b) to the light-emitting layers (113, 113 a, 113 b, and 113 c).

<Light-Emitting Layer>

The light-emitting layers (113, 113 a, 113 b, and 113 c) contain a light-emitting substance. Note that as a light-emitting substance that can be used in the light-emitting layers (113, 113 a, 113 b, and 113 c), a substance whose emission color is blue, violet, bluish violet, green, yellowish green, yellow, orange, red, or the like can be used as appropriate. When a plurality of light-emitting layers are provided, the use of different light-emitting substances for the light-emitting layers enables a structure that exhibits different emission colors (e.g., white light emission obtained by a combination of complementary emission colors). Furthermore, one light-emitting layer may have a stacked-layer structure containing different light-emitting substances.

The light-emitting layers (113, 113 a, 113 b, and 113 c) may each contain one or more kinds of organic compounds (e.g., a host material) in addition to a light-emitting substance (a guest material).

In the case where a plurality of host materials are used in the light-emitting layers (113, 113 a, 113 b, and 113 c), a second host material that is additionally used is preferably a substance having a larger energy gap than those of a known guest material and a first host material. Preferably, the lowest singlet excitation energy level (S₁ level) of the second host material is higher than that of the first host material, and the lowest triplet excitation energy level (T₁ level) of the second host material is higher than that of the guest material. Preferably, the lowest triplet excitation energy level (T₁ level) of the second host material is higher than that of the first host material. With such a structure, an exciplex can be formed by the two kinds of host materials. To form an exciplex efficiently, it is particularly preferable to combine a compound that easily accepts holes (hole-transport material) and a compound that easily accepts electrons (electron-transport material). With the above structure, high efficiency, low voltage, and a long lifetime can be achieved at the same time.

As an organic compound used as the host material (including the first host material and the second host material), organic compounds such as the hole-transport materials usable for the hole-transport layers (112, 112 a, and 112 b) described above and electron-transport materials usable for electron-transport layers (114, 114 a, and 114 b) described later can be used as long as they satisfy requirements for the host material used in the light-emitting layer. Another example is an exciplex formed by two or more kinds of organic compounds (the first host material and the second host material). An exciplex whose excited state is formed by two or more kinds of organic compounds has an extremely small difference between the S₁ level and the T₁ level and functions as a TADF material capable of converting triplet excitation energy into singlet excitation energy. In an example of a preferred combination of two or more kinds of organic compounds forming an exciplex, one compound of the two or more kinds of organic compounds has a π-electron deficient heteroaromatic ring and the other compound has a ζ-electron rich heteroaromatic ring. A phosphorescent substance such as an iridium-, rhodium-, or platinum-based organometallic complex or a metal complex may be used as one compound in the combination of compounds for forming an exciplex. The organic compound described in Embodiment 1 has an electron-transport property and thus can be efficiently used as the first host material. Furthermore, since the organic compound has a hole-transport property, it can be used as the second host material.

There is no particular limitation on the light-emitting substances that can be used for the light-emitting layers (113, 113 a, 113 b, and 113 c), and a light-emitting substance that converts singlet excitation energy into light in the visible light range or a light-emitting substance that converts triplet excitation energy into light in the visible light range can be used.

<<Light-Emitting Substance that Converts Singlet Excitation Energy into Light>>

The following substances that emit fluorescent light (fluorescent substances) can be given as examples of the light-emitting substance that converts singlet excitation energy into light and can be used in the light-emitting layers (113, 113 a, 113 b, and 113 c): a pyrene derivative, an anthracene derivative, a triphenylene derivative, a fluorene derivative, a carbazole derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a dibenzoquinoxaline derivative, a quinoxaline derivative, a pyridine derivative, a pyrimidine derivative, a phenanthrene derivative, and a naphthalene derivative. A pyrene derivative is particularly preferable because it has a high emission quantum yield. Specific examples of the pyrene derivative include N,N′-bis(3-methylphenyl)-N,N′-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N′-diphenyl-N,N′-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N′-bis(dibenzofuran-2-yl)-N,N′-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N′-bis(dibenzothiophen-2-yl)-N,N′-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N′-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N′-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine](abbreviation: 1,6BnfAPrn-02), and N,N′-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

In addition, it is possible to use, for example, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2′-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4′-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2′-bipyridine (abbreviation: PAPP2BPy), N,N′-bis[4-(9H-carbazol-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4′-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), N,N″-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N′,N′-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), and N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N′,N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA).

It is also possible to use, for example, N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(1,1′-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N′,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N′-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(1,1′-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), 1,6BnfAPrn-03, 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b′]bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b′]bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). In particular, pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 can be used, for example.

<<Light-Emitting Substance that Converts Triplet Excitation Energy into Light>>

Examples of the light-emitting substance that converts triplet excitation energy into light and can be used in the light-emitting layer 113 include substances that emit phosphorescent light (phosphorescent substances) and thermally activated delayed fluorescent (TADF) materials that exhibit thermally activated delayed fluorescence.

A phosphorescent substance is a compound that emits phosphorescent light but does not emit fluorescent light at a temperature higher than or equal to a low temperature (e.g., 77 K) and lower than or equal to room temperature (i.e., higher than or equal to 77 K and lower than or equal to 313 K). The phosphorescent substance preferably contains a metal element with large spin-orbit interaction, and can be an organometallic complex, a metal complex (platinum complex), or a rare earth metal complex, for example. Specifically, the phosphorescent substance preferably contains a transition metal element. It is preferable that the phosphorescent substance contain a platinum group element (ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), or platinum (Pt)), especially iridium, in which case the probability of direct transition between the singlet ground state and the triplet excited state can be increased.

<<Phosphorescent Substance (from 450 nm to 570 nm: Blue or Green)>>

As examples of a phosphorescent substance which emits blue or green light and whose emission spectrum has a peak wavelength in the wavelength ranging from 450 nm to 570 nm, inclusive, the following substances can be given.

Examples include organometallic complexes having a 4H-triazole ring, such as tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN²]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)₃]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)₃]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)₃]), and tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)₃]); organometallic complexes having a 1H-triazole ring, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)₃]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)₃]); organometallic complexes having an imidazole ring, such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)₃]) and tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)₃]); and organometallic complexes in which a phenylpyridine derivative having an electron-withdrawing group is a ligand, such as bis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3′,5′-bis(trifluoromethyl)phenyl]pyridinato-N,C^(2′)}iridium(III) picolinate (abbreviation: [Ir(CF₃ppy)₂(pic)]), and bis[2-(4′,6′-difluorophenyl)pyridinato-N,C^(2′)]iridium(III) acetylacetonate (abbreviation: FIr(acac)).

<<Phosphorescent Substance (from 495 nm to 590 nm: Green or Yellow)>>

As examples of a phosphorescent substance which emits green or yellow light and whose emission spectrum has a peak wavelength in the wavelength ranging from 495 nm to 590 nm, inclusive, the following substances can be given.

Examples of the phosphorescent substance include organometallic iridium complexes having a pyrimidine ring, such as tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)₃]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)₃]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)₂(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)₂(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)₂(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)₂(acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN³]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp)₂(acac)]), and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)₂(acac)]); organometallic iridium complexes having a pyrazine ring, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)₂(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)₂(acac)]); organometallic iridium complexes having a pyridine ring, such as tris(2-phenylpyridinato-N,C^(2′))iridium(III) (abbreviation: [Ir(ppy)₃]), bis(2-phenylpyridinato-N,C^(2′))iridium(III) acetylacetonate (abbreviation: [Ir(ppy)₂(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)₂(acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)₃]), tris(2-phenylquinolinato-N,C^(2′))iridium(III) (abbreviation: [Ir(pq)₃]), bis(2-phenylquinolinato-N,C^(2′))iridium(III) acetylacetonate (abbreviation: [Ir(pq)₂(acac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)₂(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], [2-d₃-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d₃-methyl-2-pyridinyl-κN²)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d₃)₂(mbfpypy-d₃)), [2-(methyl-d₃)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofuro[2,3-b]pyridin-7-yl-κC]bis[5-(methyl-d₃)-2-[5-(methyl-d₃)-2-pyridinyl-κN]phenyl-κC]iridium(III) (abbreviation: Ir(5mtpy-d6)₂(mbfpypy-iPr-d4)), [2-d₃-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)₂(mbfpypy-d₃)), and [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)₂(mdppy)); organometallic complexes such as bis(2,4-diphenyl-1,3-oxazolato-N,C^(2′))iridium(III) acetylacetonate (abbreviation: [Ir(dpo)₂(acac)]), bis{2-[4′-(perfluorophenyl)phenyl]pyridinato-N,C^(2′)}iridium(III) acetylacetonate (abbreviation: [Ir(p-PF-ph)₂(acac)]), and bis(2-phenylbenzothiazolato-N,C^(2′))iridium(III) acetylacetonate (abbreviation: [Ir(bt)₂(acac)]); and a rare earth metal complex such as tris(acetylacetonato) (monophenanthroline)terbium(III) (abbreviation: [Tb(acac)₃(Phen)]).

<<Phosphorescent Substance (from 570 nm to 750 nm: Yellow or Red)>>

As examples of a phosphorescent substance which emits yellow or red light and whose emission spectrum has a peak wavelength in the wavelength ranging from 570 nm to 750 nm, inclusive, the following substances can be given.

Examples of a phosphorescent substance include organometallic complexes having a pyrimidine ring, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)₂(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)₂(dpm)]), and (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm)₂(dpm)]); organometallic complexes having a pyrazine ring, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)₂(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)₂(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ²O,O′)iridium(III) (abbreviation: [Ir(dmdppr-P)₂(dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ²O,O′)iridium(III) (abbreviation: [Ir(dmdppr-dmCP)₂(dpm)]), bis[2-(5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN)-4,6-dimethylphenyl-κC](2,2′,6,6′-tetramethyl-3,5-heptanedionato-κ²O,O′)iridium(III) (abbreviation: [Ir(dmdppr-dmp)₂(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C^(2′)]iridium(III) (abbreviation: [Ir(mpq)₂(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C^(2′))iridium(III) (abbreviation: [Ir(dpq)₂(acac)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)₂(acac)]); organometallic complexes having a pyridine ring, such as tris(1-phenylisoquinolinato-N,C^(2′))iridium(III) (abbreviation: [Ir(piq)₃]), bis(1-phenylisoquinolinato-N,C^(2′))iridium(III) acetylacetonate (abbreviation: [Ir(piq)₂(acac)]), and bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ²O,O′)iridium(III) (abbreviation: [Ir(dmpqn)₂(acac)]); a platinum complex such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: [PtOEP]); and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)₃(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)₃(Phen)]).

<<TADF Material>>

Any of materials described below can be used as the TADF material. The TADF material is a material that has a small difference between its S₁ and T₁ levels (preferably less than or equal to 0.2 eV), enables up-conversion of a triplet excited state into a singlet excited state (i.e., reverse intersystem crossing) using a little thermal energy, and efficiently exhibits light (fluorescent light) from the singlet excited state. The thermally activated delayed fluorescence is efficiently obtained under the condition where the difference in energy between the triplet excitation energy level and the singlet excitation energy level is greater than or equal to 0 eV and less than or equal to 0.2 eV, preferably greater than or equal to 0 eV and less than or equal to 0.1 eV. Note that delayed fluorescent light by the TADF material refers to light emission having a spectrum similar to that of normal fluorescent light and an extremely long lifetime. The lifetime is longer than or equal to 1×10⁻⁶ seconds or longer than or equal to 1×10⁻³ seconds. In addition, the organic compound described in Embodiment 1 can be used.

Note that the TADF material can be also used as an electron-transport material, a hole-transport material, or a host material.

Examples of the TADF material include fullerene, a derivative thereof, an acridine derivative such as proflavine, and eosin. Other examples thereof include a metal-containing porphyrin, containing a metal such as a porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (abbreviation: SnF₂(Proto IX)), a mesoporphyrin-tin fluoride complex (abbreviation: SnF₂(Meso IX)), a hematoporphyrin-tin fluoride complex (abbreviation: SnF₂(Hemato IX)), a coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF₂(Copro III-4Me)), an octaethylporphyrin-tin fluoride complex (abbreviation: SnF₂(OEP)), an etioporphyrin-tin fluoride complex (abbreviation: SnF₂(Etio I)), and an octaethylporphyrin-platinum chloride complex (abbreviation: PtCl₂OEP).

Additionally, a heteroaromatic compound having a π-electron rich heteroaromatic compound and a π-electron deficient heteroaromatic compound may be used, such as 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10′H-spiro[acridin-9,9′-anthracen]-10′-one (abbreviation: ACRSA), 4-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)benzofuro[3,2-d]pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4PCCzPBfpm), or 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9′-phenyl-2,3′-bi-9H-carbazole (abbreviation: mPCCzPTzn-02).

Note that a substance in which a π-electron rich heteroaromatic compound is directly bonded to a π-electron deficient heteroaromatic compound is particularly preferable because both the donor property of the π-electron rich heteroaromatic compound and the acceptor property of the π-electron deficient heteroaromatic compound are improved and the energy difference between the singlet excited state and the triplet excited state becomes small. As the TADF material, a TADF material in which the singlet and triplet excited states are in thermal equilibrium (TADF100) may be used. Since such a TADF material enables a short emission lifetime (excitation lifetime), the efficiency of a light-emitting device in a high-luminance region can be less likely to decrease.

In addition to the above, another example of a material having a function of converting triplet excitation energy into light is a nano-structure of a transition metal compound having a perovskite structure. In particular, a nano-structure of a metal halide perovskite material is preferable. The nano-structure is preferably a nanoparticle or a nanorod.

As the organic compound (e.g., the host material) used in combination with the above-described light-emitting substance (guest material) in the light-emitting layers (113, 113 a, 113 b, and 113 c), one or more kinds selected from substances having a larger energy gap than the light-emitting substance (guest material) can be used.

<<Host Material for Fluorescent Light>>

In the case where the light-emitting substance used in the light-emitting layers (113, 113 a, 113 b, and 113 c) is a fluorescent substance, an organic compound (a host material) used in combination with the fluorescent substance is preferably an organic compound that has a high energy level in a singlet excited state and has a low energy level in a triplet excited state or an organic compound having a high fluorescence quantum yield. Therefore, the hole-transport material (described above) and the electron-transport material (described below) shown in this embodiment, for example, can be used as long as they are organic compounds that satisfy such a condition. In addition, the organic compound described in Embodiment 1 can be used.

In terms of a preferred combination with the light-emitting substance (fluorescent substance), examples of the organic compound (host material), some of which are mentioned in the above specific examples, include fused polycyclic aromatic compounds such as an anthracene derivative, a tetracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative, and a dibenzo[g,p]chrysene derivative.

Specific examples of the organic compound (host material) that is preferably used in combination with the fluorescent substance include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N′-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N′,N′,N″,N″,N′″,N′″-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4′-yl}anthracene (abbreviation: FLPPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,β-ADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 2,9-di(1-naphthyl)-10-phenylanthracene (abbreviation: 2αN-αNPhA), 9-(1-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: αN-mαNPAnth), 9-(2-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: ON-mαNPAnth), 9-(1-naphthyl)-10-[4-(1-naphthyl)phenyl]anthracene (abbreviation: αN-αNPAnth), 9-(2-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: ON-βNPAnth), 2-(1-naphthyl)-9-(2-naphthyl)-10-phenylanthracene (abbreviation: 2αN-βNPhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: ON-moNPAnth), 1-[4-(10-[1,1′-biphenyl]-4-yl-9-anthracenyl)phenyl]-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), 9,9′-bianthryl (abbreviation: BANT), 9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS), 9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyltetracene, and 5,12-bis(biphenyl-2-yl)tetracene.

<<Host Material for Phosphorescent Light>>

In the case where the light-emitting substance used in the light-emitting layers (113, 113 a, 113 b, and 113 c) is a phosphorescent substance, an organic compound having triplet excitation energy (an energy difference between a ground state and a triplet excited state) which is higher than that of the light-emitting substance is preferably selected as the organic compound (host material) used in combination with the phosphorescent substance. Note that when a plurality of organic compounds (e.g., a first host material and a second host material (or an assist material)) are used in combination with a light-emitting substance so that an exciplex is formed, the plurality of organic compounds are preferably mixed with the phosphorescent substance. In addition, the organic compound described in Embodiment 1 can be used.

With such a structure, light emission can be efficiently obtained by exciplex-triplet energy transfer (ExTET), which is energy transfer from an exciplex to a light-emitting substance. Note that a combination of the plurality of organic compounds that easily forms an exciplex is preferred, and it is particularly preferable to combine a compound that easily accepts holes (hole-transport material) and a compound that easily accepts electrons (electron-transport material).

In terms of a preferred combination with the light-emitting substance (phosphorescent substance), examples of the organic compounds (the host material and the assist material), some of which are mentioned in the above specific examples, include an aromatic amine (an organic compound having an aromatic amine skeleton), a carbazole derivative (an organic compound having a carbazole ring), a dibenzothiophene derivative (an organic compound having a dibenzothiophene ring), a dibenzofuran derivative (an organic compound having a dibenzofuran ring), an oxadiazole derivative (an organic compound having an oxadiazole ring), a triazole derivative (an organic compound having a triazole ring), a benzimidazole derivative (an organic compound having a benzimidazole ring), a quinoxaline derivative (an organic compound having a quinoxaline ring), a dibenzoquinoxaline derivative (an organic compound having a dibenzoquinoxaline ring), a pyrimidine derivative (an organic compound having a pyrimidine ring), a triazine derivative (an organic compound having a triazine ring), a pyridine derivative (an organic compound having a pyridine ring), a bipyridine derivative (an organic compound having a bipyridine ring), a phenanthroline derivative (an organic compound having a phenanthroline ring), a furodiazine derivative (an organic compound having a furodiazine ring), and zinc- or aluminum-based metal complexes.

Among the above organic compounds, specific examples of the aromatic amine and the carbazole derivative, which are organic compounds having a high hole-transport property, are the same as the specific examples of the hole-transport materials described above, and those materials are preferable as the host material.

Among the above organic compounds, specific examples of the dibenzothiophene derivative and the dibenzofuran derivative, which are organic compounds having a high hole-transport property, include 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), DBT3P-II, 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and 4-[3-(triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II). Such derivatives are preferable as the host material.

Other examples of preferred host materials include metal complexes having an oxazole-based or thiazole-based ligand, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

Among the above organic compounds, specific examples of the oxadiazole derivative, the triazole derivative, the benzimidazole derivative, the quinoxaline derivative, the dibenzoquinoxaline derivative, the quinazoline derivative, and the phenanthroline derivative, which are organic compounds having a high electron-transport property, include: an organic compound containing a heteroaromatic ring having a polyazole ring such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), or 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs); an organic compound containing a heteroaromatic ring having a pyridine ring such as bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), or 2,2-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline](abbreviation: mPPhen2P); 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II); 2-[3′-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II); 2-[3′-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq); 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III); 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II); 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II); 2-{4-[9,10-di(2-naphthyl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN); and 2-[4′-(9-phenyl-9H-carbazol-3-yl)-3,1′-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq). Such organic compounds are preferable as the host material.

Among the above organic compounds, specific examples of the pyridine derivative, the diazine derivative (e.g., the pyrimidine derivative, the pyrazine derivative, and the pyridazine derivative), the triazine derivative, the furodiazine derivative, which are organic compounds having a high electron-transport property, include organic compounds containing a heteroaromatic ring having a diazine ring such as 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9′-phenyl-2,3′-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), 9,9′-[pyrimidine-4,6-diylbis(biphenyl-3,3′-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)-1,1′-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 8-(1,1′-biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 9-[3′-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3′-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 11-[3′-(dibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9′,10′:4,5]furo[2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr), 11-[3′-(dibenzothiophen-4-yl)biphenyl-4-yl]phenanthro[9′,10′:4,5]furo[2,3-b]pyrazine, 11-[3′-(9H-carbazol-9-yl)biphenyl-3-yl]phenanthro[9′,10′:4,5]furo[2,3-b]pyrazine, 12-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)phenanthro[9′,10′:4,5]furo[2,3-b]pyrazine (abbreviation: 12PCCzPnfpr), 9-[(3′-9-phenyl-9H-carbazol-3-yl)biphenyl-4-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9pmPCBPNfpr), 9-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9PCCzNfpr), 10-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 10PCCzNfpr), 9-[3′-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)biphenyl-3-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9mBnfBPNfpr), 9-{3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophen-4-yl]phenyl}naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9mFDBtPNfpr), 9-[3′-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr-02), 9-[3-(9′-phenyl-3,3′-bi-9H-carbazol-9-yl)phenyl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9mPCCzPNfpr), 9-{(3′-[2,8-diphenyldibenzothiophen-4-yl)biphenyl-3-yl}naphtho[1′,2′:4,5]furo[2,3-b]pyrazine, 11-{(3′-[2,8-diphenyldibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9′,10′:4,5]furo[2,3-b]pyrazine, 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3′-(triphenylen-2-yl)-1,1′-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-[9,9′-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-[1,1′-biphenyl]-3-yl-4-phenyl-6-(8-[1,1′:4′,1″-terphenyl]-4-yl-1-dibenzofuranyl)-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 6-(1,1′-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), and 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(1,1′-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), and those materials are preferable as the host material.

Among the above organic compounds, specific examples of metal complexes that are organic compounds having a high electron-transport property include zinc- or aluminum-based metal complexes, such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq₃), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq₂), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), and bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and metal complexes having a quinoline ring or a benzoquinoline ring. Such metal complexes are preferable as the host material.

Moreover, high-molecular compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) are preferable as the host material.

Furthermore, the following organic compounds having a diazine ring, which have bipolar properties, a high hole-transport property and a high electron-transport property, can be used as the host material: 9-phenyl-9′-(4-phenyl-2-quinazolinyl)-3,3′-bi-9H-carbazole (abbreviation: PCCzQz), 2-[4′-(9-phenyl-9H-carbazol-3-yl)-3,1′-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 11-(4-[1,1′-biphenyl]-4-yl-6-phenyl-1,3,5-triazin-2-yl)-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), and 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz).

<Electron-Transport Layer>

The electron-transport layers (114, 114 a, and 114 b) transport electrons, which are injected from the second electrode 102 and the charge-generation layers (106, 106 a, and 106 b) by electron-injection layers (115, 115 a, and 115 b) described later, to the light-emitting layers (113, 113 a, and 113 b). The heat resistance of the light-emitting device of one embodiment of the present invention can be improved by including a stacked structure of electron-transport layers. The electron-transport material used in the electron-transport layers (114, 114 a, and 114 b) is preferably a substance having an electron mobility of 1×10⁻⁶ cm²/Vs or higher in the case where the square root of the electric field strength [V/cm] is 600. Note that any other substance can also be used as long as the substance has an electron-transport property higher than a hole-transport property. The electron-transport layers (114, 114 a, and 114 b) can function even with a single-layer structure and may have a stacked-layer structure including two or more layers. When a photolithography process is performed over the electron-transport layer containing the above-described mixed material, which has heat resistance, an adverse effect of the thermal process on the device characteristics can be reduced.

<<Electron-Transport Material>>

As the electron-transport material that can be used for the electron-transport layers (114, 114 a, and 114 b), an organic compound having a high electron-transport property can be used, and for example, a heteroaromatic compound can be used. The term heteroaromatic compound refers to a cyclic compound containing at least two different kinds of elements in a ring. Examples of cyclic structures include a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, and the like, among which a five-membered ring and a six-membered ring are particularly preferred. The elements contained in the heteroaromatic compound are preferably one or more of nitrogen, oxygen, and sulfur, in addition to carbon. In particular, a heteroaromatic compound containing nitrogen (a nitrogen-containing heteroaromatic compound) is preferred, and any of materials having a high electron-transport property (electron-transport materials), such as a nitrogen-containing heteroaromatic compound and a π-electron deficient heteroaromatic compound including the nitrogen-containing heteroaromatic compound, is preferably used. The compound in Embodiment 1 has an electron-transport property and thus can be used as an electron-transport material.

Note that the electron-transport material can be preferably different from the materials used in the light-emitting layer. Not all excitons formed by recombination of carriers in the light-emitting layer can contribute to light emission and some excitons are diffused into a layer in contact with the light-emitting layer or a layer in the vicinity of the light-emitting layer. In order to avoid this phenomenon, the energy level (the lowest singlet excitation energy level or the lowest triplet excitation energy level) of a material used for the layer in contact with the light-emitting layer or the layer in the vicinity of the light-emitting layer is preferably higher than that of a material used for the light-emitting layer. Therefore, when a material different from the material of the light-emitting layer is used as the electron-transport material, a light-emitting device with high efficiency can be obtained.

The heteroaromatic compound is an organic compound including at least one heteroaromatic ring.

The heteroaromatic ring includes any one of a pyridine ring, a diazine ring, a triazine ring, a polyazole ring, an oxazole ring, a thiazole ring, and the like. A heteroaromatic ring having a diazine ring includes a heteroaromatic ring having a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like. A heteroaromatic ring having a polyazole ring includes a heteroaromatic ring having an imidazole ring, a triazole ring, or an oxadiazole ring.

The heteroaromatic ring includes a fused heteroaromatic ring having a fused ring structure. Examples of the fused heteroaromatic ring include a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a quinazoline ring, a benzoquinazoline ring, a dibenzoquinazoline ring, a phenanthroline ring, a furodiazine ring, and a benzimidazole ring.

Examples of the heteroaromatic compound having a five-membered ring structure, which is a heteroaromatic compound containing carbon and one or more of nitrogen, oxygen, sulfur, and the like, include a heteroaromatic compound having an imidazole ring, a heteroaromatic compound having a triazole ring, a heteroaromatic compound having an oxazole ring, a heteroaromatic compound having an oxadiazole ring, a heteroaromatic compound having a thiazole ring, and a heteroaromatic compound having a benzimidazole ring.

Examples of the heteroaromatic compound having a six-membered ring structure, which is a heteroaromatic compound containing carbon and one or more of nitrogen, oxygen, sulfur, and the like, include a heteroaromatic compound having a heteroaromatic ring, such as a pyridine ring, a diazine ring (a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like), a triazine ring, or a polyazole ring. Other examples include a heteroaromatic compound having a bipyridine structure, a heteroaromatic compound having a terpyridine structure, and the like, which are included in examples of a heteroaromatic compound in which pyridine rings are connected.

Examples of the heteroaromatic compound having a fused ring structure partly including the above six-membered ring structure include a heteroaromatic compound having a fused heteroaromatic ring such as a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a phenanthroline ring, a furodiazine ring (including a structure in which an aromatic ring is fused to a furan ring of a furodiazine ring), or a benzimidazole ring.

Specific examples of the above-described heteroaromatic compound having a five-membered ring structure (a polyazole ring (including an imidazole ring, a triazole ring, or an oxadiazole ring), an oxazole ring, a thiazole ring, or a benzimidazole ring) include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

Specific examples of the above-described heteroaromatic compound having a six-membered ring structure (including a heteroaromatic ring having a pyridine ring, a diazine ring, a triazine ring, or the like) include: a heteroaromatic compound including a heteroaromatic ring having a pyridine ring, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) or 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB); a heteroaromatic compound including a heteroaromatic ring having a triazine ring, such as 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9′-phenyl-2,3′-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3′-(triphenylen-2-yl)-1,1′-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-[9,9′-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-[1,1′-biphenyl]-3-yl-4-phenyl-6-(8-[1,1′:4′,1″-terphenyl]-4-yl-1-dibenzofuranyl)-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), or mFBPTzn; and a heteroaromatic compound including a heteroaromatic ring having a diazine (pyrimidine) ring, such as 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 4,6mCzBP2Pm, 6-(1,1′-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(1,1′-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8PN-4mDBtPBfpm), 8BP-4mDBtPBfpm, 9mDBtBPNfpr, 9pmDBtBPNfpr, 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3′-(dibenzothiophen-4-yl)(1,1′-biphenyl-3-yl)]naphtho[1′,2′: 4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), or 8-[(2,2′-binaphthalen)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(pN2)-4mDBtPBfpm). Note that the above aromatic compounds including a heteroaromatic ring include a heteroaromatic compound having a fused heteroaromatic ring.

Other examples include heteroaromatic compounds including a heteroaromatic ring having a diazine (pyrimidine) ring, such as 2,2′-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2′-(2,2′-bipyridine-6,6′-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6′(P-Bqn)2BPy), 2,2′-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), or 6-(1,1′-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), and a heteroaromatic compound including a heteroaromatic ring having a triazine ring, such as 2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tz), or 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn).

Specific examples of the above-described heteroaromatic compound having a fused ring structure partly including a six-membered ring structure (the heteroaromatic compound having a fused ring structure) include a heteroaromatic compound having a quinoxaline ring, such as bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline](abbreviation: mPPhen2P), 2,2′-(pyridin-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)₂Py), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3′-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3′-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), or 2mpPCBPDBq.

For the electron-transport layers (114, 114 a, and 114 b), any of the metal complexes given below can be used as well as the heteroaromatic compounds described above. Examples of the metal complexes include a metal complex having a quinoline ring or a benzoquinoline ring, such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq₃), Almq₃, 8-quinolinolato-lithium (abbreviation: Liq), BeBq₂, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), or bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and a metal complex having an oxazole ring or a thiazole ring, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

High-molecular compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) can be used as the electron-transport material.

Each of the electron-transport layers (114, 114 a, and 114 b) is not limited to a single layer and may be a stack of two or more layers each containing any of the above substances.

<Electron-Injection Layer>

The electron-injection layers (115, 115 a, and 115 b) contain a substance having a high electron-injection property. The electron-injection layers (115, 115 a, and 115 b) are layers for increasing the efficiency of electron injection from the second electrode 102 and are preferably formed using a material whose value of the LUMO level has a small difference (0.5 eV or less) from the work function of a material used for the second electrode 102. Thus, the electron-injection layer 115 can be formed using an alkali metal, an alkaline earth metal, or a compound thereof, such as lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂), 8-quinolinolato-lithium (abbreviation: Liq), 2-(2-pyridyl)phenolatolithium (abbreviation: LiPP), 2-(2-pyridyl)-3-pyridinolatolithium (abbreviation: LiPPy), 4-phenyl-2-(2-pyridyl)phenolatolithium (abbreviation: LiPPP), an oxide of lithium (LiOx), or cesium carbonate. A rare earth metal such as ytterbium (Yb) and a compound of a rare earth metal such as erbium fluoride (ErF₃) can also be used. For the electron-injection layers (115, 115 a, and 115 b), a plurality of kinds of materials given above may be mixed or stacked as films. Electride may also be used for the electron-injection layers (115, 115 a, and 115 b). Examples of the electride include a substance in which electrons are added at high concentration to calcium oxide-aluminum oxide. Any of the substances used for the electron-transport layers (114, 114 a, and 114 b), which are given above, can also be used.

A mixed material in which an organic compound and an electron donor (donor) are mixed may also be used for the electron-injection layers (115, 115 a, and 115 b). Such a mixed material is excellent in an electron-injection property and an electron-transport property because electrons are generated in the organic compound by the electron donor. The organic compound here is preferably a material excellent in transporting the generated electrons; specifically, for example, the above-described electron-transport materials used for the electron-transport layers (114, 114 a, and 114 b), such as a metal complex and a heteroaromatic compound, can be used. As the electron donor, a substance showing an electron-donating property with respect to an organic compound is preferably used. Specifically, an alkali metal, an alkaline earth metal, and a rare earth metal are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like are given. In addition, an alkali metal oxide and an alkaline earth metal oxide are preferable, and lithium oxide, calcium oxide, barium oxide, and the like are given. Alternatively, a Lewis base such as magnesium oxide can be used. Further alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used. Alternatively, a stack of two or more of these materials may be used.

A mixed material in which an organic compound and a metal are mixed may also be used for the electron-injection layers (115, 115 a, and 115 b). The organic compound used here preferably has a LUMO level higher than or equal to −3.6 eV and lower than or equal to −2.3 eV. Moreover, a material having an unshared electron pair is preferable.

Thus, as the organic compound used in the above mixed material, a mixed material obtained by mixing a metal and the heteroaromatic compound given above as the material that can be used for the electron-transport layer may be used. Preferred examples of the heteroaromatic compound include materials having an unshared electron pair, such as a heteroaromatic compound having a five-membered ring structure (e.g., an imidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, or a benzimidazole ring), a heteroaromatic compound having a six-membered ring structure (e.g., a pyridine ring, a diazine ring (including a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like), a triazine ring, a bipyridine ring, or a terpyridine ring), and a heteroaromatic compound having a fused ring structure partly including a six-membered ring structure (e.g., a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, or a phenanthroline ring). Since the materials are specifically described above, description thereof is omitted here.

As a metal used for the above mixed material, a transition metal that belongs to Group 5, Group 7, Group 9, or Group 11 or a material that belongs to Group 13 in the periodic table is preferably used, and examples thereof include Ag, Cu, Al, and In. Here, the organic compound forms a singly occupied molecular orbital (SOMO) with the transition metal.

To amplify light obtained from the light-emitting layer 113 b, for example, the optical path length between the second electrode 102 and the light-emitting layer 113 b is preferably less than one fourth of the wavelength k of light emitted from the light-emitting layer 113 b. In that case, the optical path length can be adjusted by changing the thickness of the electron-transport layer 114 b or the electron-injection layer 115 b.

When the charge-generation layer 106 is provided between the two EL layers (103 a and 103 b) as in the light-emitting device in FIG. 1D, a structure in which a plurality of EL layers are stacked between the pair of electrodes (the structure is also referred to as a tandem structure) can be obtained.

<Charge-Generation Layer>

The charge-generation layer 106 has a function of injecting electrons into the EL layer 103 a and injecting holes into the EL layer 103 b when voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge-generation layer 106 may be either a p-type layer in which an electron acceptor (acceptor) is added to a hole-transport material or an electron-injection buffer layer in which an electron donor (donor) is added to an electron-transport material. Alternatively, both of these layers may be stacked. Furthermore, an electron-relay layer may be provided between the p-type layer and the electron-injection buffer layer. Note that forming the charge-generation layer 106 with the use of any of the above materials can inhibit an increase in driving voltage in the stack of the EL layers.

In the case where the charge-generation layer 106 is a p-type layer in which an electron acceptor is added to a hole-transport material, which is an organic compound, any of the materials described in this embodiment can be used as the hole-transport material. Examples of the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F₄-TCNQ) and chloranil. Other examples include oxides of metals that belong to Group 4 to Group 8 of the periodic table. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide. Any of the above-described acceptor materials may be used. Furthermore, a mixed film obtained by mixing materials of a p-type layer or a stack of films containing the respective materials may be used.

In the case where the charge-generation layer 106 an electron-injection buffer layer in which an electron donor is added to an electron-transport material, any of the materials described in this embodiment can be used as the electron-transport material. As the electron donor, it is possible to use an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Group 2 or Group 13 of the periodic table, or an oxide or a carbonate thereof. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (Li₂O), cesium carbonate, or the like is preferably used. An organic compound such as tetrathianaphthacene may be used as the electron donor.

When an electron-relay layer is provided between a p-type layer and an electron-injection buffer layer in the charge-generation layer 106, the electron-relay layer contains at least a substance having an electron-transport property and has a function of preventing an interaction between the electron-injection buffer layer and the p-type layer and transferring electrons smoothly. The LUMO level of the substance having an electron-transport property in the electron-relay layer is preferably between the LUMO level of the acceptor substance in the p-type layer and the LUMO level of the substance having an electron-transport property in the electron-transport layer in contact with the charge-generation layer 106. Specifically, the LUMO level of the substance having an electron-transport property in the electron-relay layer is preferably higher than or equal to −5.0 eV, further preferably higher than or equal to −5.0 eV and lower than or equal to −3.0 eV. Note that as the substance having an electron-transport property in the electron-relay layer, a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand is preferably used.

Although FIG. 1D illustrates the structure in which two EL layers 103 are stacked, three or more EL layers may be stacked with charge-generation layers each provided between two adjacent EL layers.

<<Cap Layer>

Although not illustrated in FIGS. 1A to 1E, a cap layer may be provided over the second electrode 102 of the light-emitting device. For example, a material with high refractive index can be used for the cap layer. When the cap layer is provided over the second electrode 102, extraction efficiency of light emitted from the second electrode 102 can be improved.

Specific examples of a material that can be used for the cap layer include 5,5′-diphenyl-2,2′-di-5H-[1]benzothieno[3,2-c]carbazole (abbreviation: BisBTc), and 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II). In addition, the organic compound described in Embodiment 1 can be used.

<Substrate>

The light-emitting device described in this embodiment can be formed over a variety of substrates. Note that the type of substrate is not limited to a certain type. Examples of the substrate include semiconductor substrates (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate including stainless steel foil, a tungsten substrate, a substrate including tungsten foil, a flexible substrate, an attachment film, paper including a fibrous material, and a base material film.

Examples of the glass substrate include a barium borosilicate glass substrate, an aluminoborosilicate glass substrate, and a soda lime glass substrate. Examples of the flexible substrate, the attachment film, and the base material film include plastics typified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyether sulfone (PES), a synthetic resin such as acrylic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, epoxy resin, an inorganic vapor deposition film, and paper.

For fabrication of the light-emitting device in this embodiment, a gas phase method such as an evaporation method or a liquid phase method such as a spin coating method or an ink-jet method can be used. When an evaporation method is used, a physical vapor deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam evaporation method, a molecular beam evaporation method, or a vacuum evaporation method, a chemical vapor deposition method (CVD method), or the like can be used. Specifically, the layers having various functions (the hole-injection layer 111, the hole-transport layer 112, the light-emitting layer 113, the electron-transport layer 114, and the electron-injection layer 115) included in the EL layers of the light-emitting device can be formed by an evaporation method (e.g., a vacuum evaporation method), a coating method (e.g., a dip coating method, a die coating method, a bar coating method, a spin coating method, or a spray coating method), a printing method (e.g., an ink-jet method, screen printing (stencil), offset printing (planography), flexography (relief printing), gravure printing, or micro-contact printing), or the like.

In the case where a film formation method such as the coating method or the printing method is employed, a high-molecular compound (e.g., an oligomer, a dendrimer, or a polymer), a middle-molecular compound (a compound between a low-molecular compound and a high-molecular compound with a molecular weight of 400 to 4000), an inorganic compound (e.g., a quantum dot material), or the like can be used. The quantum dot material can be a colloidal quantum dot material, an alloyed quantum dot material, a core-shell quantum dot material, a core quantum dot material, or the like.

Materials that can be used for the layers (the hole-injection layer 111, the hole-transport layer 112, the light-emitting layer 113, the electron-transport layer 114, and the electron-injection layer 115) included in the EL layer 103 of the light-emitting device described in this embodiment are not limited to the materials described in this embodiment, and other materials can be used in combination as long as the functions of the layers are fulfilled.

Note that in this specification and the like, the terms “layer” and “film” can be interchanged with each other as appropriate.

The structures described in this embodiment can be used in combination with any of the structures described in the other embodiments as appropriate.

Embodiment 3

This embodiment will describe a light-emitting and light-receiving apparatus 700 as a specific example of a light-emitting and light-receiving apparatus of one embodiment of the present invention and an example of the manufacturing method. The light-emitting and light-receiving apparatus 700 includes a light-emitting device and thus can be regarded as a light-emitting apparatus; includes a light-receiving device and thus can be regarded as a light-receiving apparatus; and can be used in a display unit in an electronic device and thus can be regarded as a display panel or a display device.

<Structure Example of Light-Emitting and Light-Receiving Apparatus 700>

A light-emitting and light-receiving apparatus 700 illustrated in FIG. 2A includes a light-emitting device 550B, a light-emitting device 550G, a light-emitting device 550R, and a light-receiving device 550PS. The light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS are formed over a functional layer 520 provided over a first substrate 510. The functional layer 520 includes, for example, driver circuits such as a gate driver and a source driver that are composed of a plurality of transistors, and wirings that electrically connect these circuits. Note that these driver circuits are electrically connected to the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS, for example, to drive them. The light-emitting and light-receiving apparatus 700 includes an insulating layer 705 over the functional layer 520 and the devices (the light-emitting devices and the light-receiving device), and the insulating layer 705 has a function of attaching a second substrate 770 and the functional layer 520.

The light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R include the device structure described in Embodiment 2, and the light-receiving device 550PS has a device structure described later in Embodiment 8. In other words, the EL layer 103 illustrated in FIG. 2A is different in each light-emitting device. Note that although in this embodiment, the case where the devices (a plurality of light-emitting devices and a light-receiving device) are formed separately is described, part of an EL layer of a light-emitting device (a hole-injection layer, a hole-transport layer, or an electron-transport layer) and part of an active layer of a light-receiving device (a first transport layer or a second transport layer) may be formed using the same material at the same time in the manufacturing process. The detailed description will be made in Embodiment 8.

In this specification and the like, a structure in which light-emitting layers in light-emitting devices of different colors (for example, blue (B), green (G), and red (R)) and a light-receiving layer in a light-receiving device are separately formed or separately patterned is sometimes referred to as a side-by-side (SBS) structure. Although the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS are arranged in this order in the light-emitting and light-receiving apparatus 700 illustrated in FIG. 2A, one embodiment of the present invention is not limited to this structure. For example, in the light-emitting and light-receiving apparatus 700, these devices may be arranged in the order of the light-emitting device 550R, the light-emitting device 550G, the light-emitting device 550B, and the light-receiving device 550PS.

In FIG. 2A, the light-emitting device 550B includes an electrode 551B, the electrode 552, and an EL layer 103B. The light-emitting device 550G includes an electrode 551G, the electrode 552, and an EL layer 103G. The light-emitting device 550R includes an electrode 551R, the electrode 552, and an EL layer 103R. The light-receiving device 550PS includes an electrode 551PS, the electrode 552, and a light-receiving layer 103PS. Note that a specific structure of each layer of the light-receiving device is as described in Embodiment 2. In addition, a specific structure of each layer of the light-emitting device is as described in Embodiment 8. The EL layer 103B, the EL layer 103G, and the EL layer 103R each have a stacked-layer structure of layers having different functions including their respective light-emitting layers (105B, 105G, and 105R). The light-receiving layer 103PS has a stacked-layer structure of layers having different functions including an active layer 105PS. FIG. 2A illustrates a case where the EL layer 103B includes a hole-injection/transport layer 104B, the light-emitting layer 105B, an electron-transport layer 108B, and an electron-injection layer 109; the EL layer 103G includes a hole-injection/transport layer 104G, the light-emitting layer 105G, an electron-transport layer 108G, and the electron-injection layer 109; the EL layer 103R includes a hole-injection/transport layer 104R, the light-emitting layer 105R, an electron-transport layer 108R, and the electron-injection layer 109; and the light-receiving layer 103PS includes a first transport layer 104PS, the active layer 105PS, a second transport layer 108PS, and the electron-injection layer 109. However, the present invention is not limited thereto. Note that each of the hole-injection/transport layers (104B, 104G, and 104R) represents a layer having the functions of the hole-injection layer and the hole-transport layer described in Embodiment 2, and may have a stacked-layer structure.

Note that the electron-transport layers (108B, 108G, and 108R) and the second transport layer 108PS may have a function of blocking holes moving from the anode side to the cathode side through the light-emitting layers (105B, 105G, and 105R) and the active layer 105PS of the light-receiving device. The electron-injection layer 109 may have a stacked-layer structure in which some or all of layers are formed using different materials.

As illustrated in FIG. 2A, the insulating layer 107 may be formed on side surfaces (or end portions) of the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105B, 105G, and 105R), and the electron-transport layers (108B, 108G, and 108R) included in the EL layers (103B, 103G, and 103R), and side surfaces (or end portions) of the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS included in the light-receiving layer 103PS. The insulating layer 107 is formed in contact with the side surfaces (or the end portions) of the EL layers (103B, 103G, and 103R) and the light-receiving layer 103PS. This can inhibit entry of oxygen, moisture, or constituent elements thereof into the inside through the side surfaces of the EL layers (103B, 103G, and 103R) and the light-receiving layer 103PS. For the insulating layer 107, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon nitride oxide can be used, for example. Some of the above-described materials may be stacked to form the insulating layer 107. The insulating layer 107 can be formed by a sputtering method, a CVD method, an MBE method, a PLD method, an ALD method, or the like and is formed preferably by an ALD method, which achieves favorable coverage. Note that the insulating layer 107 continuously covers the side surfaces (or the end portions) of parts of the EL layers (103B, 103G, and 103R) and parts of the light-receiving layer 103PS of adjacent devices. For example, in FIG. 2A, the side surfaces of parts of the EL layer 103B of the light-emitting device 550B and the EL layer 103G of the light-emitting device 550G are covered with the insulating layer 107. In regions covered with the insulating layer 107, partition walls 528 formed using an insulating material are preferably formed, as illustrated in FIG. 2A.

In addition, the electron-injection layer 109 is formed over the electron-transport layers (108B, 108G, and 108R) that are parts of the EL layers (103B, 103G, and 103R), the second transport layer 108PS that is part of the light-receiving layer 103PS, and the insulating layer 107. Note that the electron-injection layer 109 may have a stacked-layer structure of two or more layers (for example, stacked layers having different electric resistances).

The electrode 552 is formed over the electron-injection layer 109. Note that the electrodes (551B, 551G, and 551R) and the electrode 552 include overlap regions. The light-emitting layer 105B is provided between the electrode 551B and the electrode 552, the light-emitting layer 105G is provided between the electrode 551G and the electrode 552, the light-emitting layer 105R is provided between the electrode 551R and the electrode 552, and the light-receiving layer 103PS is provided between the electrode 551PS and the electrode 552.

The EL layers (103B, 103G, and 103R) illustrated in FIG. 2A each have a structure similar to that of the EL layer 103 described in Embodiment 2. The light-receiving layer 103PS has a structure similar to that of a light-receiving layer described later in Embodiment 8. The light-emitting layer 105B can emit blue light, the light-emitting layer 105G can emit green light, and the light-emitting layer 105R can emit red light, for example.

The partition walls 528 are provided in regions surrounded by the electron-injection layer 109 and the insulating layer 107. As illustrated in FIG. 2A, the partition walls 528 are in contact with the side surfaces (or the end portions) of parts of the electrodes (551B, 551G, 551R, and 551PS), the EL layers (103B, 103G, and 103R), and the light-receiving layer 103PS with the insulating layer 107 therebetween.

In each of the EL layers and the light-receiving layer, particularly the hole-injection layer, which is included in the hole-transport region between the anode and the light-emitting layer and between the anode and the active layer, often has high conductivity; thus, a hole-injection layer formed as a layer shared by adjacent devices might cause crosstalk. Thus, as described in this structure example, the partition walls 528 formed using an insulating material are provided between the EL layers and between the EL layer and the light-receiving layer, which can inhibit occurrence of crosstalk between adjacent devices.

In the manufacturing method described in this embodiment, side surfaces (or end portions) of the EL layer and the light-receiving layer are exposed in the patterning step. This may promote deterioration of the EL layer and the light-receiving layer by allowing the entry of oxygen, water, or the like through the side surfaces (or the end portions) of the EL layer and the light-receiving layer. Hence, providing the partition wall 528 can inhibit the deterioration of the EL layer and the light-receiving layer in the manufacturing process.

Providing the partition wall 528 can flatten the surface by reducing a depressed portion formed between adjacent devices. When the depressed portion is reduced, disconnection of the electrode 552 formed over the EL layers and the light-receiving layer can be inhibited. Examples of an insulating material used to form the partition wall 528 include organic materials such as an acrylic resin, a polyimide resin, an epoxy resin, an imide resin, a polyamide resin, a polyimide-amide resin, a silicone resin, a siloxane resin, a benzocyclobutene-based resin, a phenol resin, and precursors of these resins. Other examples include organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinyl pyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, and alcohol-soluble polyamide resin. A photosensitive resin such as a photoresist can also be used. Examples of the photosensitive resin include positive-type materials and negative-type materials.

With the use of the photosensitive resin, the partition wall 528 can be fabricated by only light exposure and developing steps. The partition wall 528 may be fabricated using a negative photosensitive resin (e.g., a resist material). In the case where an insulating layer containing an organic material is used as the partition wall 528, a material absorbing visible light is suitably used. When such a material absorbing visible light is used for the partition wall 528, light emission from the EL layer can be absorbed by the partition wall 528, leading to a reduction in light leakage (stray light) to an adjacent EL layer or light-receiving layer. Accordingly, a display panel with high display quality can be provided.

For example, the difference between the top-surface level of the partition wall 528 and the top-surface level of any of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS is preferably 0.5 times or less, further preferably 0.3 times or less the thickness of the partition wall 528. The partition wall 528 may be provided such that the top-surface level of any of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS is higher than the top-surface level of the partition wall 528, for example. Alternatively, the partition wall 528 may be provided such that the top-surface level of the partition wall 528 is higher than the top-surface level of any of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS, for example.

When electrical continuity is established between the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS in a light-emitting and light-receiving apparatus (display panel) with a high resolution more than 1000 ppi, crosstalk occurs, resulting in a narrower color gamut that the light-emitting and light-receiving apparatus is capable of reproducing. Providing the partition wall 528 in a high-resolution display panel with more than 1000 ppi, preferably more than 2000 ppi, or further preferably in an ultrahigh-resolution display panel with more than 5000 ppi allows the display panel to express vivid colors.

FIGS. 2B and 2C are each a schematic top view of the light-emitting and light-receiving apparatus 700 taken along the dashed-dotted line Ya-Yb in the cross-sectional view of FIG. 2A. Specifically, the light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R are arranged in a matrix. Note that FIG. 2B illustrates what is called a stripe arrangement, in which the light-emitting devices of the same color are arranged in the X-direction. FIG. 2C illustrates a structure in which the light-emitting devices of the same color are arranged in the X-direction and separated by patterning for each pixel. Note that the arrangement method of the light-emitting devices is not limited thereto; another method such as a delta, zigzag, PenTile, or diamond arrangement may also be used.

The EL layers (103B, 103G, and 103R) and the light-receiving layer 103PS are processed to be separated by patterning using a photolithography method; hence, a light-emitting and light-receiving apparatus (display panel) with a high resolution can be fabricated. The side surfaces (end portions) of the layers of the EL layer processed by patterning using a photolithography method have substantially the same surface (or are positioned on substantially the same plane). In addition, the end portions (side surfaces) of the layers of the light-receiving layer processed by patterning using a photolithography method have substantially the same surface (or are positioned on substantially the same plane). In this case, the widths (SE) of spaces 580 between the EL layers and between the EL layer and the light-receiving layer are each preferably 5 μm or less, further preferably 1 μm or less.

In the EL layer, particularly the hole-injection layer, which is included in the hole-transport region between the anode and the light-emitting layer, often has high conductivity; thus, a hole-injection layer formed as a layer shared by adjacent light-emitting devices might cause crosstalk. Therefore, processing the EL layers to be separated by patterning using a photolithography method as described in this structure example can suppress occurrence of crosstalk between adjacent light-emitting devices.

FIG. 2D is a schematic cross-sectional view taken along the dashed-dotted line C1-C2 in FIGS. 2B and 2C. FIG. 2D illustrates a connection portion 130 where a connection electrode 551C and the electrode 552 are electrically connected to each other. In the connection portion 130, the electrode 552 is provided over and in contact with the connection electrode 551C. The partition wall 528 is provided to cover an end portion of the connection electrode 551C.

<Example of Method for Manufacturing Light-Emitting and Light-Receiving Apparatus>

The electrode 551B, the electrode 551G, the electrode 551R, and the electrode 551PS are formed as illustrated in FIG. 3A. For example, a conductive film is formed over the functional layer 520 over the first substrate 510 and processed into predetermined shapes by a photolithography method.

The conductive film can be formed by any of a sputtering method, a chemical vapor deposition (CVD) method, a molecular beam epitaxy (MBE) method, a vacuum evaporation method, a pulsed laser deposition (PLD) method, an atomic layer deposition (ALD) method, and the like. Examples of the CVD method include a plasma-enhanced chemical vapor deposition (PECVD) method and a thermal CVD method. An example of a thermal CVD method is a metal organic CVD (MOCVD) method.

The conductive film may be processed by a nanoimprinting method, a sandblasting method, a lift-off method, or the like as well as a photolithography method described above. Alternatively, island-shaped thin films may be directly formed by a film formation method using a shielding mask such as a metal mask.

There are two typical examples of photolithography methods. In one of the methods, a resist mask is formed over a thin film to be processed, the thin film is processed by etching or the like, and then the resist mask is removed. In the other method, a photosensitive thin film is formed and then processed into a desired shape by light exposure and development. The former method involves heat treatment steps such as pre-applied bake (PAB) after resist application and post-exposure bake (PEB) after light exposure. In one embodiment of the present invention, a lithography method is used not only for processing of a conductive film but also for processing of a thin film used for formation of an EL layer (a film made of an organic compound or a film partly containing an organic compound).

As light for exposure in a photolithography method, it is possible to use light with the i-line (wavelength: 365 nm), light with the g-line (wavelength: 436 nm), light with the h-line (wavelength: 405 nm), or light in which the i-line, the g-line, and the h-line are mixed. Alternatively, ultraviolet light, KrF laser light, ArF laser light, or the like can be used. Exposure may be performed by liquid immersion exposure technique. As the light for exposure, extreme ultraviolet (EUV) light or X-rays may also be used. Instead of the light for exposure, an electron beam can be used. It is preferable to use EUV, X-rays, or an electron beam because extremely minute processing can be performed. Note that a photomask is not needed when light exposure is performed by scanning with a beam such as an electron beam.

For etching of a thin film using a resist mask, a dry etching method, a wet etching method, a sandblasting method, or the like can be used.

Subsequently, as illustrated in FIG. 3B, the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B are formed over the electrode 551B, the electrode 551G, the electrode 551R, and the electrode 551PS. Note that the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B can be formed using a vacuum evaporation method, for example. Furthermore, a sacrifice layer 110B is formed over the electron-transport layer 108B. For the formation of the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B, any of the materials described in Embodiment 2 can be used.

For the sacrifice layer 110B, it is preferable to use a film highly resistant to etching treatment performed on the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B, i.e., a film having high etching selectivity with respective to the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B. The sacrifice layer 110B preferably has a stacked-layer structure of a first sacrifice layer and a second sacrifice layer which have different etching selectivities. For the sacrifice layer 110B, it is possible to use a film that can be removed by a wet etching method, which causes less damage to the EL layer 103B. In wet etching, oxalic acid or the like can be used as an etching material.

For the sacrifice layer 110B, an inorganic film such as a metal film, an alloy film, a metal oxide film, a semiconductor film, or an inorganic insulating film can be used, for example. The sacrifice layer 110B can be formed by any of a variety of film formation methods such as a sputtering method, an evaporation method, a CVD method, and an ALD method.

For the sacrifice layer 110B, a metal material such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, or tantalum or an alloy material containing the metal material can be used, for example. It is particularly preferable to use a low-melting-point material such as aluminum or silver.

A metal oxide such as indium gallium zinc oxide (also referred to as In—Ga—Zn oxide or IGZO) can be used for the sacrifice layer 110B. It is also possible to use indium oxide, indium zinc oxide (In—Zn oxide), indium tin oxide (In—Sn oxide), indium titanium oxide (In—Ti oxide), indium tin zinc oxide (In—Sn—Zn oxide), indium titanium zinc oxide (In—Ti—Zn oxide), indium gallium tin zinc oxide (In—Ga—Sn—Zn oxide), or the like. Alternatively, indium tin oxide containing silicon can also be used, for example.

An element M (M is one or more of aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium) may be used instead of gallium. In particular, M is preferably one or more of gallium, aluminum, and yttrium.

For the sacrifice layer 110B, an inorganic insulating material such as aluminum oxide, hafnium oxide, or silicon oxide can be used.

The sacrifice layer 110B is preferably formed using a material that can be dissolved in a solvent chemically stable with respect to the electron-transport layer 108B that is in the uppermost position. Specifically, a material that can be dissolved in water or alcohol can be suitably used for the sacrifice layer 110B. In formation of the sacrifice layer 110B, preferably, application of such a material dissolved in a solvent such as water or alcohol is performed by a wet process, followed by heat treatment for evaporating the solvent. At this time, the heat treatment is preferably performed under a reduced-pressure atmosphere, in which case the solvent can be removed at a low temperature in a short time and thermal damage to the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B can be accordingly reduced.

In the case where the sacrifice layer 110B having a stacked-layer structure is formed, the stacked-layer structure can include the first sacrifice layer formed using any of the above-described materials and the second sacrifice layer thereover.

The second sacrifice layer in that case is a film used as a hard mask for etching of the first sacrifice layer. In processing the second sacrifice layer, the first sacrifice layer is exposed. Thus, a combination of films having greatly different etching rates is selected for the first sacrifice layer and the second sacrifice layer. Thus, a film that can be used for the second sacrifice layer can be selected in accordance with the etching conditions of the first sacrifice layer and those of the second sacrifice layer.

For example, in the case where the second sacrifice layer is etched by dry etching using a fluorine-containing gas (also referred to as a fluorine-based gas), the second sacrifice layer can be formed using silicon, silicon nitride, silicon oxide, tungsten, titanium, molybdenum, tantalum, tantalum nitride, an alloy containing molybdenum and niobium, an alloy containing molybdenum and tungsten, or the like. Here, a film of a metal oxide such as IGZO or ITO can be given as an example of a film having a high etching selectivity to the second sacrifice layer (i.e., a film with a low etching rate) in the dry etching using the fluorine-based gas, and can be used for the first sacrifice layer.

Note that the material for the second sacrifice layer is not limited to the above and can be selected from a variety of materials in accordance with the etching conditions of the first sacrifice layer and those of the second sacrifice layer. For example, any of the films that can be used for the first sacrifice layer can be used for the second sacrifice layer.

For the second sacrifice layer, a nitride film can be used, for example. Specifically, it is possible to use a nitride such as silicon nitride, aluminum nitride, hafnium nitride, titanium nitride, tantalum nitride, tungsten nitride, gallium nitride, or germanium nitride.

Alternatively, an oxide film can be used for the second sacrifice layer. Typically, it is possible to use a film of an oxide or an oxynitride such as silicon oxide, silicon oxynitride, aluminum oxide, aluminum oxynitride, hafnium oxide, or hafnium oxynitride.

Next, as illustrated in FIG. 3C, a resist is applied onto the sacrifice layer 110B, and the resist having a desired shape (a resist mask REG) is formed by a photolithography method. Such a method involves heat treatment steps such as pre-applied bake (PAB) after the resist application and post-exposure bake (PEB) after light exposure. The temperature reaches approximately 100° C. during the PAB, and approximately 120° C. during the PEB, for example. Therefore, the light-emitting device should be resistant to such high treatment temperatures.

Next, part of the sacrifice layer 110B that is not covered with the resist mask REG is removed by etching using the resist mask REG, the resist mask REG is removed, and then the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B that are not covered with the sacrifice layer 110B are partly removed by etching, so that the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B are processed to have side surfaces (or have their side surfaces exposed) over the electrode 551B or have belt-like shapes extending in the direction intersecting the sheet of the diagram. Note that dry etching is preferably employed for the etching. Note that in the case where the sacrifice layer 110B has the aforementioned stacked-layer structure of the first sacrifice layer and the second sacrifice layer, the hole-injection/transport layer 104B, the light-emitting layer 105B, and the electron-transport layer 108B may be processed into a predetermined shape in the following manner: part of the second sacrifice layer is etched using the resist mask REG, the resist mask REG is then removed, and part of the first sacrifice layer is etched using the second sacrifice layer as a mask. The structure illustrated in FIG. 4A is obtained through these etching steps.

Subsequently, as illustrated in FIG. 4B, the hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G are formed over the sacrifice layer 110B, the electrode 551G, the electrode 551R, and the electrode 551PS. The hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G can be formed using any of the materials described in Embodiment 2. Note that the hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G can be formed by a vacuum evaporation method, for example.

Next, as illustrated in FIG. 4C, the sacrifice layer 110G is formed over the electron-transport layer 108G, a resist is applied onto the sacrifice layer 110G, and the resist having a desired shape (the resist mask REG) is formed by a photolithography method. Part of the sacrifice layer 110G that is not covered with the obtained resist mask REG is removed by etching, the resist mask REG is removed, and then parts of the hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G that are not covered with the sacrifice layer 110G are removed by etching. Thus, the hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G are processed to have side surfaces (or have their side surfaces exposed) over the electrode 551G or have belt-like shapes extending in the direction perpendicular to the sheet of the diagram. Note that dry etching is preferably employed for the etching. Note that the sacrifice layer 110G can be formed using a material similar to that for the sacrifice layer 110B. In the case where the sacrifice layer 110G has the aforementioned stacked-layer structure of the first sacrifice layer and the second sacrifice layer, the hole-injection/transport layer 104G, the light-emitting layer 105G, and the electron-transport layer 108G may be processed into a predetermined shape in the following manner: part of the second sacrifice layer is etched using the resist mask REG, the resist mask REG is then removed, and part of the first sacrifice layer is etched using the second sacrifice layer as a mask. The structure illustrated in FIG. 5A is obtained through these etching steps.

Next, as illustrated in FIG. 5B, the hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R are formed over the sacrifice layer 110B, the sacrifice layer 110G, the electrode 551R, and the electrode 551PS. The hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R can be formed using any of the materials described in Embodiment 2. The hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R can be formed by a vacuum evaporation method, for example.

Next, as illustrated in FIG. 5C, the sacrifice layer 110R is formed over the electron-transport layer 108R, a resist is applied onto the sacrifice layer 110R, and the resist having a desired shape (the resist mask REG) is formed by a photolithography method. Part of the sacrifice layer 110R that is not covered with the obtained resist mask REG is removed by etching, the resist mask REG is removed, and then parts of the hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R that are not covered with the sacrifice layer 110R are removed by etching. Thus, the hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R are processed to have side surfaces (or have their side surfaces exposed) over the electrode 551R or have belt-like shapes extending in the direction intersecting the sheet of the diagram. Note that dry etching is preferably employed for the etching. Note that the sacrifice layer 110R can be formed using a material similar to that for the sacrifice layer 110B. In the case where the sacrifice layer 110R has the aforementioned stacked-layer structure of the first sacrifice layer and the second sacrifice layer, the hole-injection/transport layer 104R, the light-emitting layer 105R, and the electron-transport layer 108R may be processed into a predetermined shape in the following manner: part of the second sacrifice layer is etched using the resist mask REG, the resist mask REG is then removed, and part of the first sacrifice layer is etched using the second sacrifice layer as a mask. The structure illustrated in FIG. 6A is obtained through these etching steps.

Next, as illustrated in FIG. 6B, the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS are formed over the sacrifice layer 110B, the sacrifice layer 110G, the sacrifice layer 110R, and the electrode 551PS. As a material for forming the first transport layer 104PS, for example, the material for the hole-injection layer and the hole-transport layer of the light-emitting device described in Embodiment 2 can be used. As a material for the active layer 105PS, a material described in Embodiment 8 can be used. Furthermore, as a material for forming the second transport layer 108PS, for example, the material for the electron-transport layer and the electron-injection layer described in Embodiment 2 can be used. Note that the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS can be formed by a vacuum evaporation method, for example.

Next, as illustrated in FIG. 6C, the sacrifice layer 110PS is formed over the second transport layer 108PS, a resist is applied onto the sacrifice layer 110PS, and the resist having a desired shape (the resist mask REG) is formed by a photolithography method. Part of the sacrifice layer 110PS that is not covered with the obtained resist mask REG is removed by etching, the resist mask REG is removed, and then the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS that are not covered with the sacrifice layer 110PS are partly removed by etching. Thus, the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS are processed to have side surfaces (or have their side surfaces exposed) over the electrode 551PS or have belt-like shapes extending in the direction intersecting the sheet of the diagram. Note that dry etching is preferably employed for the etching. Note that the sacrifice layer 110PS can be formed using a material similar to that for the sacrifice layer 110B. In the case where the sacrifice layer 110PS has the aforementioned stacked-layer structure of the first sacrifice layer and the second sacrifice layer, the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS may be processed into a predetermined shape in the following manner: part of the second sacrifice layer is etched using the resist mask REG, the resist mask REG is then removed, and part of the first sacrifice layer is etched using the second sacrifice layer as a mask. The structure illustrated in FIG. 6D is obtained through these etching steps.

Next, as illustrated in FIG. 7A, the insulating layer 107 is formed over the sacrifice layers 110B, 110G, 110R, and 110PS.

Note that the insulating layer 107 can be formed by an ALD method, for example. In this case, as illustrated in FIG. 7A, the insulating layer 107 is formed to be in contact with the side surfaces (end portions) of the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105B, 105G, and 105R), and the electron-transport layers (108B, 108G, and 108R) of the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving device. This can inhibit entry of oxygen, moisture, or constituent elements thereof into the inside through the side surfaces of the layers. Examples of the material used for the insulating layer 107 include aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, and silicon nitride oxide.

Then, as illustrated in FIG. 7B, after part of the insulating layer 107 and the sacrifice layers (110B, 110G, 110R, and 110PS) are removed, the electron-injection layer 109 is formed over the insulating layer 107, the electron-transport layers (108B, 108G, and 108R), and the second transport layer 108PS. The electron-injection layer 109 can be formed using any of the materials described in Embodiment 2. The electron-injection layer 109 is formed by a vacuum evaporation method, for example. Note that the electron-injection layer 109 is in contact with the side surfaces (end portions) of the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105R, 105G, and 105B), and the electron-transport layers (108B, 108G, and 108R) of the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving device with the insulating layer 107 therebetween.

Next, as illustrated in FIG. 7C, the electrode 552 is formed. The electrode 552 is formed by a vacuum evaporation method, for example. The electrode 552 is formed over the electron-injection layer 109. Note that the electrode 552 is in contact with the side surfaces (end portions) of the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105B, 105G, and 105R), and the electron-transport layers (108B, 108G, and 108R) of the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving device with the electron-injection layer 109 and the insulating layer 107 therebetween. This can prevent electrical short circuits between the electrode 552 and each of the following layers: the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105B, 105G, and 105R), and the electron-transport layers (108B, 108G, and 108R) of the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving device.

Through the above steps, the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS in the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS can be processed to be separated from each other.

The EL layers (103B, 103G, and 103R) and the light-receiving layer 103PS are processed to be separated by patterning using a photolithography method; hence, a light-emitting and light-receiving apparatus (display panel) with a high resolution can be fabricated. Side surfaces (end portions) of the layers of the EL layer processed by patterning using a photolithography method have substantially the same surface (or are positioned on substantially the same plane). In addition, the end portions (side surfaces) of the layers of the light-receiving layer processed by patterning using a photolithography method have substantially the same surface (or are positioned on substantially the same plane).

Each of the hole-injection/transport layers (104B, 104G, and 104R) of the EL layers and the first transport layer 104PS of the light-receiving layer often has high conductivity, and thus might cause crosstalk when formed as a layer shared by adjacent devices. Therefore, processing the EL layers to be separated by patterning using a photolithography method as described in this structure example can inhibit occurrence of crosstalk between adjacent light-emitting devices and adjacent light-receiving devices.

In this structure example, the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105B, 105G, and 105R), and the electron-transport layers (108B, 108G, and 108R) of the EL layers (103B, 103G, and 103R) included in the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving layer 103PS included in the light-receiving device are processed to be separated by patterning using a photolithography method; thus, the end portions (side surfaces) of the processed EL layer have substantially the same surface (or are positioned on substantially the same plane). In addition, the side surfaces (end portions) of the layers of the light-receiving layer processed by patterning using a photolithography method have substantially the same surface (or are positioned on substantially the same plane).

In addition, the hole-injection/transport layers (104B, 104G, and 104R), the light-emitting layers (105R, 105G, and 105B), and the electron-transport layers (108B, 108G, and 108R) of the EL layers (103B, 103G, and 103R) included in the light-emitting devices and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving layer 103PS included in the light-receiving device are processed to be separated by patterning using a photolithography method. Thus, the space 580 is provided between the processed end portions (side surfaces) of adjacent light-emitting devices. In FIG. 7C, when the space 580 is denoted by a distance SE between the EL layers or between the EL layer and the light-receiving layer of adjacent devices, decreasing the distance SE increases the aperture ratio and the resolution. By contrast, as the distance SE is increased, the effect of the difference in the fabrication process between the adjacent light-emitting devices becomes permissible, which leads to an increase in manufacturing yield. Since the light-emitting device and the light-receiving device fabricated according to this specification are suitable for a miniaturization process, the distance SE between the EL layers or between the EL layer and the light-receiving layer of adjacent light-emitting devices can be longer than or equal to 0.5 μm and shorter than or equal to 5 μm, preferably longer than or equal to 1 μm and shorter than or equal to 3 μm, further preferably longer than or equal to 1 μm and shorter than or equal to 2.5 μm, and still further preferably longer than or equal to 1 μm and shorter than or equal to 2 μm. Typically, the distance SE is preferably longer than or equal to 1 μm and shorter than or equal to 2 μm (e.g., 1.5 μm or a neighborhood thereof).

In this specification and the like, a device formed using a metal mask or a fine metal mask (FMM) is sometimes referred to as a device having a metal mask (MM) structure. In this specification and the like, a device formed without using a metal mask or an FMM is sometimes referred to as a device having a metal maskless (MML) structure. Since a light-emitting and light-receiving apparatus having the MML structure is formed without using a metal mask, the pixel arrangement, the pixel shape, and the like can be designed more flexibly than in a light-emitting and light-receiving apparatus having the FMM structure or the MM structure.

Note that the island-shaped EL layers of the light-emitting and light-receiving apparatus having the MML structure are formed by not patterning using a metal mask but processing after deposition of an EL layer. Thus, a light-emitting and light-receiving apparatus with a higher resolution or a higher aperture ratio than a conventional one can be achieved. Moreover, EL layers can be formed separately for each color, which enables extremely clear images; thus, a light-emitting and light-receiving apparatus with a high contrast and high display quality can be achieved. Furthermore, provision of a sacrifice layer over an EL layer can reduce damage on the EL layer during the manufacturing process and increase the reliability of the light-emitting device.

In FIG. 2A and FIG. 7C, the widths of the EL layers (103B, 103G, and 103R) are substantially equal to those of the electrodes (551B, 551G, and 551R) in the light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R, and the width of the light-receiving layer 103PS is substantially equal to that of the electrode 551PS in the light-receiving device 550PS; however, one embodiment of the present invention is not limited thereto.

In the light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R, the widths of the EL layers (103B, 103G, and 103R) may be smaller than those of the electrodes (551B, 551G, and 551R). In the light-receiving device 550PS, the width of the light-receiving layer 103PS may be smaller than that of the electrode 551PS. FIG. 7D illustrates an example in which the widths of the EL layers (103B and 103G) are smaller than those of the electrodes (551B and 551G) in the light-emitting devices 550B and 550G.

In the light-emitting devices 550B, 550G, and 550R, the widths of the EL layers (103B, 103G, and 103R) may be larger than those of the electrodes (551B, 551G, and 551R). In the light-receiving device 550PS, the width of the light-receiving layer 103PS may be larger than that of the electrode 551PS. FIG. 7E illustrates an example in which the width of the EL layer 103R is larger than that of the electrode 551R in the light-emitting device 550R.

The structures described in this embodiment can be used in combination with any of the structures described in the other embodiments as appropriate.

Embodiment 4

In this embodiment, an apparatus 720 is described with reference to FIGS. 8A to 8F, FIGS. 9A to 9C, and FIG. 10 . The apparatus 720 illustrated in FIGS. 8A to 8F, FIGS. 9A to 9C, and FIG. 10 includes any of the light-emitting devices described in Embodiment 2 and therefore is a light-emitting apparatus. Furthermore, the apparatus 720 described in this embodiment can be used in a display unit of an electronic device or the like and therefore can also be referred to as a display panel or a display device. Moreover, when the apparatus 720 includes the light-emitting device as a light source and a light-receiving device that can receive light from the light-emitting device, the apparatus 720 can be referred to as a light-emitting and light-receiving apparatus. Note that the light-emitting apparatus, the display panel, the display device, and the light-emitting and light-receiving apparatus each include at least a light-emitting device.

Furthermore, the light-emitting apparatus, the display panel, the display device, and the light-emitting and light-receiving apparatus of this embodiment can each have high definition or a large size. Therefore, the light-emitting apparatus, the display panel, the display device, and the light-emitting and light-receiving apparatus of this embodiment can be used, for example, in display units of electronic devices such as a digital camera, a digital video camera, a digital photo frame, a mobile phone, a portable game console, a smart phone, a wristwatch terminal, a tablet terminal, a portable information terminal, and an audio reproducing apparatus, in addition to display units of electronic devices with a relatively large screen, such as a television device, a desktop or laptop personal computer, a monitor of a computer or the like, digital signage, and a large game machine such as a pachinko machine.

FIG. 8A is a top view of the apparatus 720 (e.g., the light-emitting apparatus, the display panel, the display device, and the light-emitting and light-receiving apparatus).

In FIG. 8A, the apparatus 720 has a structure in which a substrate 710 and a substrate 711 are attached to each other. In addition, the apparatus 720 includes a display region 701, a circuit 704, a wiring 706, and the like. Note that the display region 701 includes a plurality of pixels. As illustrated in FIG. 8B, a pixel 703(i, j) illustrated in FIG. 8A and a pixel 703(i+1, j) are adjacent to each other.

Furthermore, in the example of the apparatus 720 illustrated in FIG. 8A, the substrate 710 is provided with an integrated circuit (IC) 712 by a chip on glass (COG) method, a chip on film (COF) method, or the like. As the IC 712, an IC including a scan line driver circuit, a signal line driver circuit, or the like can be used, for example. In the example illustrated in FIG. 8A, an IC including a signal line driver circuit is used as the IC 712, and a scan line driver circuit is used as the circuit 704.

The wiring 706 has a function of supplying signals and power to the display region 701 and the circuit 704. The signals and power are input to the wiring 706 from the outside through a flexible printed circuit (FPC) 713 or to the wiring 706 from the IC 712. Note that the apparatus 720 is not necessarily provided with the IC. The IC may be mounted on the FPC by a COF method or the like.

FIG. 8B illustrates the pixel 703(i, j) and the pixel 703(i+1, j) of the display region 701. A plurality of kinds of subpixels including light-emitting devices that emit different color light from each other can be included in the pixel 703(i, j). Alternatively, a plurality of subpixels including light-emitting devices that emit the same color light may be included in addition to those described above. In the case where a plurality of kinds of subpixels including light-emitting devices that emit different color light from each other are included in the pixel, three kinds of subpixels can be included, for example. The three subpixels can be of three colors of red (R), green (G), and blue (B) or of three colors of yellow (Y), cyan (C), and magenta (M), for example. Alternatively, the pixel can include four kinds of subpixels. The four subpixels can be of four colors of R, G, B, and white (W) or of four colors of R, G, B, and Y, for example. Specifically, the pixel 703(i, j) can consist of a subpixel 702B(i, j) for blue display, a subpixel 702G(i, j) for green display, and a subpixel 702R(i, j) for red display.

The 720 includes not only a subpixel including a light-emitting device, but also a subpixel including a light-receiving device.

FIGS. 8C to 8E illustrate various layout examples of the pixel 703(i, j) including a subpixel 702PS(i, j) including a light-receiving device. The pixel arrangement in FIG. 8C is stripe arrangement, and the pixel arrangement in FIG. 8D is matrix arrangement. The pixel arrangement in FIG. 8E has a structure where three subpixels (the subpixels R, G, and PS) are vertically arranged next to one subpixel (the subpixel B).

Furthermore, as illustrated in FIG. 8F, a subpixel 702IR(i, j) that emits infrared rays may be added to any of the above-described sets of subpixels in the pixel 703(i, j). In the pixel arrangement in FIG. 8F, the vertically oriented three subpixels G, B, and R are arranged laterally, and the subpixel PS and the horizontally oriented subpixel IR are arranged laterally below the three subpixels. Specifically, the subpixel 702IR(i, j) that emits light including light with a wavelength ranging from 650 nm to 1000 nm, inclusive, may be used in the pixel 703(i, j). Note that the wavelength of light detected by the subpixel 702PS(i, j) is not particularly limited; however, the light-receiving device included in the subpixel 702PS(i, j) preferably has sensitivity to light emitted by the light-emitting device included in the subpixel 702R(i, j), the subpixel 702G(i, j), the subpixel 702B(i, j), or the subpixel 702IR(i, j). For example, the light-receiving device preferably detects one or more kinds of light in blue, violet, bluish violet, green, yellowish green, yellow, orange, red, and infrared wavelength ranges, for example.

Note that the arrangement of subpixels is not limited to the structures illustrated in FIGS. 8B to 8F and a variety of arrangement methods can be employed. The arrangement of subpixels may be stripe arrangement, S stripe arrangement, matrix arrangement, delta arrangement, Bayer arrangement, or pentile arrangement, for example.

Furthermore, top surfaces of the subpixels may have a triangular shape, a quadrangular shape (including a rectangular shape and a square shape), a polygonal shape such as a pentagonal shape, a polygonal shape with rounded corners, an elliptical shape, or a circular shape, for example. The top surface shape of a subpixel herein refers to a top surface shape of a light-emitting region of a light-emitting device.

Furthermore, in the case where not only a light-emitting device but also a light-receiving device is included in a pixel, the pixel has a light-receiving function and thus can detect a contact or approach of an object while displaying an image. For example, an image can be displayed by using all the subpixels included in a light-emitting apparatus; or light can be emitted by some of the subpixels as a light source and an image can be displayed by using the remaining subpixels.

Note that the light-receiving area of the subpixel 702PS(i, j) is preferably smaller than the light-emitting areas of the other subpixels. A smaller light-receiving area leads to a narrower image-capturing range, inhibits a blur in a captured image, and improves the definition. Thus, by using the subpixel 702PS(i, j), high-resolution or high-definition image capturing is possible. For example, image capturing for personal authentication with the use of a fingerprint, a palm print, the iris, the shape of a blood vessel (including the shape of a vein and the shape of an artery), a face, or the like is possible by using the subpixel 702PS(i, j).

Moreover, the subpixel 702PS(i, j) can be used in a touch sensor (also referred to as a direct touch sensor), a near touch sensor (also referred to as a hover sensor, a hover touch sensor, a contactless sensor, or a touchless sensor), or the like. For example, the subpixel 702PS(i, j) preferably detects infrared light. Thus, touch sensing is possible even in a dark place.

Here, the touch sensor or the near touch sensor can detect an approach or contact of an object (e.g., a finger, a hand, or a pen). The touch sensor can detect the object when the light-emitting and light-receiving apparatus and the object come in direct contact with each other. Furthermore, the near touch sensor can detect the object even when the object is not in contact with the light-emitting and light-receiving apparatus. For example, the light-emitting and light-receiving apparatus can preferably detect the object when the distance between the light-emitting and light-receiving apparatus and the object is more than or equal to 0.1 mm and less than or equal to 300 mm, preferably more than or equal to 3 mm and less than or equal to 50 mm. With this structure, the light-emitting and light-receiving apparatus can be controlled without the object directly contacting with the light-emitting and light-receiving apparatus. In other words, the light-emitting and light-receiving apparatus can be controlled in a contactless (touchless) manner. With the above-described structure, the light-emitting and light-receiving apparatus can be controlled with a reduced risk of being dirty or damaged, or without direct contact between the object and a dirt (e.g., dust, bacteria, or a virus) attached to the light-emitting and light-receiving apparatus.

For high-resolution image capturing, the subpixel 702PS(i, j) is preferably provided in every pixel included in the light-emitting and light-receiving apparatus. Meanwhile, in the case where the subpixel 702PS(i, j) is used in a touch sensor, a near touch sensor, or the like, high accuracy is not required as compared to the case of capturing an image of a fingerprint or the like; accordingly, the subpixel 702PS(i, j) is provided in some subpixels in the light-emitting and light-receiving apparatus. When the number of subpixels 702PS(i, j) included in the light-emitting and light-receiving apparatus is smaller than the number of subpixels 702R(i, j) or the like, higher detection speed can be achieved.

Next, an example of a pixel circuit of a subpixel included in the light-emitting device is described with reference to FIG. 9A. A pixel circuit 530 illustrated in FIG. 9A includes a light-emitting device (EL) 550, a transistor M15, a transistor M16, a transistor M17, and a capacitor C3. Note that a light-emitting diode can be used as the light-emitting device 550. In particular, any of the light-emitting devices described in Embodiment 2 is preferably used as the light-emitting device 550.

In FIG. 9A, a gate of the transistor M15 is electrically connected to a wiring VG, one of a source and a drain of the transistor M15 is electrically connected to a wiring VS, and the other of the source and the drain of the transistor M15 is electrically connected to one electrode of the capacitor C3 and a gate of the transistor M16. One of a source and a drain of the transistor M16 is electrically connected to a wiring V4, and the other is electrically connected to an anode of the light-emitting device 550 and one of a source and a drain of the transistor M17. A gate of the transistor M17 is electrically connected to a wiring MS, and the other of the source and the drain of the transistor M17 is electrically connected to a wiring OUT2. A cathode of the light-emitting device 550 is electrically connected to a wiring V5.

A constant potential is supplied to the wiring V4 and the wiring V5. In the light-emitting device 550, the anode side can have a high potential and the cathode side can have a lower potential than the anode side. The transistor M15 is controlled by a signal supplied to the wiring VG and functions as a selection transistor for controlling a selection state of the pixel circuit 530. The transistor M16 functions as a driving transistor that controls a current flowing through the light-emitting device 550 in accordance with a potential supplied to the gate of the transistor M16. When the transistor M15 is on, a potential supplied to the wiring VS is supplied to the gate of the transistor M16, and the luminance of the light-emitting device 550 can be controlled in accordance with the potential. The transistor M17 is controlled by a signal supplied to the wiring MS and has a function of outputting a potential between the transistor M16 and the light-emitting device 550 to the outside through the wiring OUT2.

Here, a transistor in which a metal oxide (an oxide semiconductor) is used as a semiconductor layer where a channel is formed is preferably used as transistors M15, M16, and M17 included in a pixel circuit 530 in FIG. 9A and the transistors M11, M12, M13, and M14 included in the pixel circuit 531 in FIG. 9B.

A transistor using a metal oxide having a wider band gap and a lower carrier density than silicon can achieve an extremely low off-state current. Such a low off-state current enables retention of charges accumulated in a capacitor that is connected in series to the transistor for a long time. Therefore, it is particularly preferable to use a transistor containing an oxide semiconductor as the transistors M11, M12, and M15 each of which is connected in series to a capacitor C2 or the capacitor C3. When each of the other transistors also includes an oxide semiconductor, manufacturing cost can be reduced.

Alternatively, transistors using silicon as a semiconductor in which a channel is formed can be used as the transistors M11 to M17. In particular, it is preferable to use silicon with high crystallinity such as single crystal silicon or polycrystalline silicon because high field-effect mobility can be achieved and higher-speed operation can be performed.

Alternatively, a transistor containing an oxide semiconductor may be used as at least one of the transistors M11 to M17, and transistors containing silicon may be used as the other transistors.

Next, an example of a pixel circuit of a subpixel including a light-receiving device is described with reference to FIG. 9B. The pixel circuit 531 illustrated in FIG. 9B includes a light-receiving device (PD) 560, the transistor M11, the transistor M12, the transistor M13, the transistor M14, and the capacitor C2. For example, a photodiode is used as the light-receiving device (PD) 560.

In FIG. 9B, an anode of the light-receiving device (PD) 560 is electrically connected to a wiring V1, and a cathode of the light-receiving device (PD) 560 is electrically connected to one of a source and a drain of the transistor M11. A gate of the transistor M11 is electrically connected to a wiring TX, and the other of the source and the drain of the transistor M11 is electrically connected to one electrode of the capacitor C2, one of a source and a drain of the transistor M12, and a gate of the transistor M13. A gate of the transistor M12 is electrically connected to a wiring RES, and the other of the source and the drain of the transistor M12 is electrically connected to a wiring V2. One of a source and a drain of the transistor M13 is electrically connected to a wiring V3, and the other of the source and the drain of the transistor M13 is electrically connected to one of a source and a drain of the transistor M14. A gate of the transistor M14 is electrically connected to a wiring SE1, and the other of the source and the drain of the transistor M14 is electrically connected to a wiring OUT1.

A constant potential is supplied to the wiring V1, the wiring V2, and the wiring V3. When the light-receiving device (PD) 560 is driven with a reverse bias, the wiring V2 is supplied with a potential higher than the potential of the wiring V1. The transistor M12 is controlled by a signal supplied to the wiring RES and has a function of resetting the potential of a node connected to the gate of the transistor M13 to a potential supplied to the wiring V2. The transistor M11 is controlled by a signal supplied to the wiring TX and has a function of controlling the timing at which the potential of the node changes, in accordance with a current flowing through the light-receiving device (PD) 560. The transistor M13 functions as an amplifier transistor for outputting a signal corresponding to the potential of the node. The transistor M14 is controlled by a signal supplied to the wiring SE1 and functions as a selection transistor for reading an output corresponding to the potential of the node by an external circuit connected to the wiring OUT1.

Although n-channel transistors are illustrated in FIGS. 9A and 9B, p-channel transistors can be used instead.

The transistors included in the pixel circuit 530 and the transistors included in the pixel circuit 531 are preferably formed side by side over the same substrate. Preferably, the transistors included in the pixel circuit 530 and the transistors included in the pixel circuit 531 are periodically arranged in one region, in particular.

One or more layers including the transistor and/or the capacitor are preferably provided to overlap with the light-receiving device (PD) 560 or the light-emitting device (EL) 550. Thus, the effective area of each pixel circuit can be reduced, and a high-resolution light-receiving unit or display unit can be achieved.

FIG. 9C illustrates an example of a specific structure of a transistor that can be used in the pixel circuit described with reference to FIGS. 9A and 9B. As the transistor, a bottom-gate transistor, a top-gate transistor, or the like can be used as appropriate.

The transistor illustrated in FIG. 9C includes a semiconductor film 508, a conductive film 504, an insulating film 506, a conductive film 512A, and a conductive film 512B. The transistor is formed over an insulating film 501C, for example. The transistor also includes an insulating film 516 (an insulating film 516A and an insulating film 516B) and an insulating film 518.

The semiconductor film 508 includes a region 508A electrically connected to the conductive film 512A and a region 508B electrically connected to the conductive film 512B. The semiconductor film 508 includes a region 508C between the region 508A and the region 508B.

The conductive film 504 includes a region overlapping with the region 508C and has a function of a gate electrode.

The insulating film 506 includes a region positioned between the semiconductor film 508 and the conductive film 504. The insulating film 506 has a function of a first gate insulating film.

The conductive film 512A has one of a function of a source electrode and a function of a drain electrode, and the conductive film 512B has the other thereof.

A conductive film 524 can be used in the transistor. The semiconductor film 508 is sandwiched between the conductive film 504 and a region included in the conductive film 524. The conductive film 524 has a function of a second gate electrode. An insulating film 501D is positioned between the semiconductor film 508 and the conductive film 524 and has a function of a second gate insulating film.

The insulating film 516 functions as, for example, a protective film covering the semiconductor film 508. Specifically, a film including a silicon oxide film, a silicon oxynitride film, a silicon nitride oxide film, a silicon nitride film, an aluminum oxide film, a hafnium oxide film, an yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, or a neodymium oxide film can be used as the insulating film 516, for example.

For the insulating film 518, a material that has a function of inhibiting diffusion of oxygen, hydrogen, water, an alkali metal, an alkaline earth metal, and the like is preferably used. Specifically, the insulating film 518 can be formed using silicon nitride, silicon oxynitride, aluminum nitride, or aluminum oxynitride, for example. In each of silicon oxynitride and aluminum oxynitride, the number of nitrogen atoms contained is preferably larger than the number of oxygen atoms contained.

Note that in a step of forming the semiconductor film used in the transistor of the pixel circuit, the semiconductor film used in the transistor of the driver circuit can be formed. A semiconductor film having the same composition as the semiconductor film used in the transistor of the pixel circuit can be used in the driver circuit, for example.

The semiconductor film 508 preferably contains indium, M (M is one or more of gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium), and zinc, for example. Specifically, M is preferably one or more of aluminum, gallium, yttrium, and tin.

In particular, an oxide containing indium (In), gallium (Ga), and zinc (Zn) (also referred to as IGZO) is preferably used as the semiconductor film 508. Alternatively, it is preferable to use an oxide containing indium, tin, and zinc. Further alternatively, it is preferable to use an oxide containing indium, gallium, tin, and zinc. Further alternatively, it is preferable to use an oxide containing indium (In), aluminum (Al), and zinc (Zn) (also referred to as IAZO). Further alternatively, it is preferable to use an oxide containing indium (In), aluminum (Al), gallium (Ga), and zinc (Zn) (also referred to as IAGZO).

When the semiconductor film is an In-M-Zn oxide, the atomic ratio of In is preferably greater than or equal to the atomic ratio of M in the In-M-Zn oxide. Examples of the atomic ratio of the metal elements in such an In-M-Zn oxide are In:M:Zn=1:1:1, 1:1:1.2, 1:3:2, 1:3:4, 2:1:3, 3:1:2, 4:2:3, 4:2:4.1, 5:1:3, 5:1:6, 5:1:7, 5:1:8, 6:1:6, and 5:2:5 and a composition in the vicinity of any of the above atomic ratios. Note that the vicinity of the atomic ratio includes ±30% of an intended atomic ratio.

For example, in the case of describing an atomic ratio of In:Ga:Zn=4:2:3 or a composition in the vicinity thereof, the case is included in which with the atomic proportion of In being 4, the atomic proportion of Ga is greater than or equal to 1 and less than or equal to 3 and the atomic proportion of Zn is greater than or equal to 2 and less than or equal to 4. In the case of describing an atomic ratio of In:Ga:Zn=5:1:6 or a composition in the vicinity thereof, the case is included in which with the atomic proportion of In being 5, the atomic proportion of Ga is greater than 0.1 and less than or equal to 2 and the atomic proportion of Zn is greater than or equal to 5 and less than or equal to 7. In the case of describing an atomic ratio of In:Ga:Zn=1:1:1 or a composition in the vicinity thereof, the case is included in which with the atomic proportion of In being 1, the atomic proportion of Ga is greater than 0.1 and less than or equal to 2 and the atomic proportion of Zn is greater than 0.1 and less than or equal to 2.

There is no particular limitation on the crystallinity of a semiconductor material used in the transistor, and an amorphous semiconductor or a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor partly including crystal regions) can be used. It is preferable to use a semiconductor having crystallinity, in which case deterioration of transistor characteristics can be suppressed.

A semiconductor layer of a transistor preferably contains a metal oxide (also referred to as an oxide semiconductor). As an oxide semiconductor having crystallinity, a c-axis aligned crystalline oxide semiconductor (CAAC-OS), a nanocrystalline oxide semiconductor (nc-OS), and the like are given.

Alternatively, a transistor using silicon in its channel formation region (a Si transistor) may be used. Examples of silicon include single crystal silicon (single crystal Si), polycrystalline silicon, and amorphous silicon. In particular, a transistor containing low-temperature polysilicon (LTPS) in its semiconductor layer (hereinafter also referred to as an LTPS transistor) can be used. The LTPS transistor has high field-effect mobility and excellent frequency characteristics.

With the use of Si transistors such as LTPS transistors, a circuit required to be driven at a high frequency (e.g., a source driver circuit) can be formed on the same substrate as the display unit. This allows simplification of an external circuit mounted on the light-emitting apparatus and a reduction in costs of parts and mounting costs.

An OS transistor has much higher field-effect mobility than a transistor containing amorphous silicon. In addition, the OS transistor has an extremely low leakage current between a source and a drain in an off state (hereinafter also referred to as off-state current), and charge accumulated in a capacitor that is connected in series to the transistor can be held for a long period. Furthermore, the power consumption of the light-emitting apparatus can be reduced with the OS transistor.

The off-state current per micrometer of channel width of the OS transistor at room temperature can be lower than or equal to 1 aA (1×10⁻¹⁸ A), lower than or equal to 1 zA (1×10⁻²¹ A), or lower than or equal to 1 yA (1×10⁻²⁴ A). Note that the off-state current per micrometer of channel width of a Si transistor at room temperature is higher than or equal to 1 fA (1×10⁻¹⁵ A) and lower than or equal to 1 pA (1×10⁻¹² A). In other words, the off-state current of the OS transistor is lower than that of the Si transistor by approximately ten orders of magnitude.

To increase the luminance of the light-emitting device included in the pixel circuit, the amount of current fed through the light-emitting device needs to be increased. To increase the current amount, the source-drain voltage of a driving transistor included in the pixel circuit needs to be increased. An OS transistor has a higher withstand voltage between a source and a drain than a Si transistor; hence, high voltage can be applied between the source and the drain of the OS transistor. Thus, with use of an OS transistor as a driving transistor included in the pixel circuit, the amount of current flowing through the light-emitting device can be increased, resulting in an increase in emission luminance of the light-emitting device.

When transistors operate in a saturation region, a change in source-drain current relative to a change in gate-source voltage can be smaller in an OS transistor than in a Si transistor. Accordingly, when an OS transistor is used as the driving transistor in the pixel circuit, a current flowing between the source and the drain can be set minutely in accordance with a change in gate-source voltage; hence, the amount of current flowing through the light-emitting device can be controlled. Consequently, the number of gray levels expressed by the pixel circuit can be increased.

Regarding saturation characteristics of current flowing when transistors operates in a saturation region, even in the case where the source-drain voltage of an OS transistor increases gradually, a more stable current (saturation current) can be fed through the OS transistor than through a Si transistor. Thus, by using an OS transistor as the driving transistor, a stable current can be fed through light-emitting devices even when the current-voltage characteristics of the light-emitting devices vary, for example. In other words, when the OS transistor operates in the saturation region, the source-drain current hardly changes with an increase in the source-drain voltage; hence, the luminance of the light-emitting device can be stable.

As described above, with use of an OS transistor as a driving transistor included in the pixel circuit, it is possible to achieve “inhibition of black floating”, “increase in emission luminance”, “increase in gray level”, “inhibition of variation in light-emitting devices”, and the like.

The semiconductor film used in the transistor of the driver circuit can be formed in the same step as the semiconductor film used in the transistor of the pixel circuit. The driver circuit can be formed over a substrate where the pixel circuit is formed. The number of components of an electronic device can be reduced.

Alternatively, silicon may be used for the semiconductor film 508. Examples of silicon include single crystal silicon, polycrystalline silicon, and amorphous silicon. In particular, a transistor containing low-temperature polysilicon (LTPS) in its semiconductor layer (hereinafter also referred to as an LTPS transistor) is preferably used. The LTPS transistor has high field-effect mobility and excellent frequency characteristics.

With the use of transistors using silicon such as LTPS transistors, a circuit required to be driven at a high frequency (e.g., a source driver circuit) can be formed on the same substrate as the display unit. This allows simplification of an external circuit mounted on the light-emitting apparatus and a reduction in costs of parts and mounting costs.

It is preferable to use a transistor containing a metal oxide (hereinafter also referred to as an oxide semiconductor) in a semiconductor layer where a channel is formed (hereinafter such a transistor is also referred to as an OS transistor) as at least one of the transistors included in the pixel circuit. An OS transistor has much higher field-effect mobility than a transistor containing amorphous silicon. In addition, the OS transistor has an extremely low leakage current between a source and a drain in an off state (hereinafter also referred to as off-state current), and charge accumulated in a capacitor that is connected in series to the transistor can be held for a long period. Furthermore, the power consumption of the light-emitting apparatus can be reduced with the OS transistor.

When an LTPS transistor is used as one or more of the transistors included in the pixel circuit and an OS transistor is used as the rest, the light-emitting apparatus can have low power consumption and high driving capability. As a favorable example, it is preferable that an OS transistor be used as a transistor functioning as a switch for controlling electrical continuity between wirings and an LTPS transistor be used as a transistor for controlling current, for instance. A structure where an LTPS transistor and an OS transistor are used in combination may be referred to as LTPO. The use of LTPO enables the display panel to have low power consumption and high drive capability.

For example, one of the transistors included in the pixel circuit functions as a transistor for controlling a current flowing through the light-emitting device and can be referred to as a driving transistor. One of a source and a drain of the driving transistor is electrically connected to the pixel electrode of the light-emitting device. An LTPS transistor is preferably used as the driving transistor. Accordingly, the amount of current flowing through the light-emitting device can be increased in the pixel circuit.

Another transistor included in the pixel circuit functions as a switch for controlling selection and non-selection of the pixel and can be referred to as a selection transistor. A gate of the selection transistor is electrically connected to a gate line, and one of a source and a drain thereof is electrically connected to a source line (signal line). An OS transistor is preferably used as the selection transistor. Accordingly, the gray level of the pixel can be maintained even with an extremely low frame frequency (e.g., 1 fps or less); thus, power consumption can be reduced by stopping the driver in displaying a still image.

In the case of using an oxide semiconductor in a semiconductor film, the apparatus 720 includes a light-emitting device including an oxide semiconductor in its semiconductor film and having a metal maskless (MML) structure. With this structure, the leakage current that might flow through the transistor and the leakage current that might flow between adjacent light-emitting devices (also referred to as a lateral leakage current, a side leakage current, or the like) can become extremely low. With the structure, a viewer can observe any one or more of the image crispness, the image sharpness, a high chroma, and a high contrast ratio in an image displayed on the display device. When the leakage current that might flow through the transistor and the lateral leakage current that might flow between light-emitting devices are extremely low, display with little leakage of light at the time of black display (what is called black floating) (such display is also referred to as deep black display) can be achieved.

In particular, in the case where a light-emitting device having an MML structure employs the above-described SBS structure, a layer provided between light-emitting devices (for example, also referred to as an organic layer or a common layer which is shared by the light-emitting devices) is disconnected; accordingly, display with no or extremely small lateral leakage can be achieved.

The structure of the transistors used in the display panel may be selected as appropriate depending on the size of the screen of the display panel. For example, single crystal Si transistors can be used in the display panel with a screen diagonal greater than or equal to 0.1 inches and less than or equal to 3 inches. In addition, LTPS transistors can be used in the display panel with a screen diagonal greater than or equal to 0.1 inches and less than or equal to 30 inches, preferably greater than or equal to 1 inch and less than or equal to 30 inches. In addition, an LTPO structure (where an LTPS transistor and an OS transistor are used in combination) can be used for the display panel with a screen diagonal greater than or equal to 0.1 inches and less than or equal to 50 inches, preferably greater than or equal to 1 inch and less than or equal to 50 inches. In addition, OS transistors can be used in the display panel with a screen diagonal greater than or equal to 0.1 inches and less than or equal to 200 inches, preferably greater than or equal to 50 inches and less than or equal to 100 inches.

With the use of single crystal Si transistors, an increase in screen size is extremely difficult due to the size of a single crystal Si substrate. Furthermore, since a laser crystallization apparatus is used in the fabrication process, LTPS transistors are unlikely to respond to an increase in screen size (typically to a screen diagonal greater than 30 inches). By contrast, since the fabrication process does not necessarily require a laser crystallization apparatus or the like or can be performed at a relatively low temperature (typically, lower than or equal to 450° C.), OS transistors can be applied to a display panel with a relatively large area (typically, a screen diagonal greater than or equal to 50 inches and less than or equal to 100 inches). In addition, LTPO can be applied to a display panel with a size (typically, a screen diagonal of 1 to 50 inches inclusive) midway between the structure using LTPS transistors and the structure using OS transistors.

Next, a cross-sectional view of a light-emitting and light-receiving apparatus is shown. FIG. 10 is a cross-sectional view of the light-emitting and light-receiving apparatus illustrated in FIG. 8A.

FIG. 10 is a cross-sectional view of part of a region including the FPC 713 and the wiring 706 and part of the display region 701 including the pixel 703(i, j).

In FIG. 10 , the light-emitting and light-receiving apparatus 700 includes the functional layer 520 between the first substrate 510 and the second substrate 770. The functional layer 520 includes, as well as the above-described transistors (M11, M12, M13, M14, M15, M16, and M17), the capacitors (C2 and C3), and the like described with reference to FIGS. 9A to 9C, wirings (VS, VG, V1, V2, V3, V4, and V5) electrically connected to these components, for example. FIG. 10 illustrates a non-limiting example of the functional layer 520 that includes a pixel circuit 530X(i, j), a pixel circuit 530S(i, j), and a driver circuit GD.

Furthermore, each pixel circuit included in the functional layer 520 is electrically connected to a light-emitting device or a light-receiving device. For example, in FIG. 10 , the pixel circuit 530X(i, j) and the pixel circuit 530S(i, j) included in the functional layer 520 are electrically connected to a light-emitting device 550X(i, j) and a light-receiving device 550S(i, j), respectively, in FIG. 10 formed over the functional layer 520. Concretely, the light-emitting device 550X(i, j) is electrically connected to the pixel circuit 530X(i, j) through a wiring 591X, and the light-receiving device 550S(i, j) is electrically connected to the pixel circuit 530S(i, j) through a wiring 591S. The insulating layer 705 is provided over the functional layer 520, the light-emitting devices, and the light-receiving device, and has a function of attaching the second substrate 770 and the functional layer 520.

As the second substrate 770, a substrate where touch sensors are arranged in a matrix can be used. For example, a substrate provided with capacitive touch sensors or optical touch sensors can be used as the second substrate 770. Thus, the light-emitting and light-receiving apparatus of one embodiment of the present invention can be used as a touch panel.

The structures described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

Embodiment 5

This embodiment will describe structures of electronic devices of embodiments of the present invention with reference to FIGS. 11A to 11E, FIGS. 12A to 12E, and FIGS. 13A and 13B.

FIGS. 11A to 11E, FIGS. 12A to 12E, and FIGS. 13A and 13B each illustrate a structure of an electronic device of one embodiment of the present invention. FIG. 11A is a block diagram of an electronic device, and FIGS. 11B to 11E are perspective views illustrating structures of the electronic device. FIGS. 12A to 12E are perspective views illustrating structures of electronic devices. FIGS. 13A and 13B are perspective views illustrating structures of electronic devices.

An electronic device 5200B described in this embodiment includes an arithmetic device 5210 and an input/output device 5220 (see FIG. 11A).

The arithmetic device 5210 has a function of receiving handling data and a function of supplying image data on the basis of the handling data.

The input/output device 5220 includes a display unit 5230, an input unit 5240, a sensor unit 5250, and a communication unit 5290, and has a function of supplying handling data and a function of receiving image data. The input/output device 5220 also has a function of supplying sensing data, a function of supplying communication data, and a function of receiving communication data.

The input unit 5240 has a function of supplying handling data. For example, the input unit 5240 supplies handling data on the basis of handling by a user of the electronic device 5200B.

Specifically, a keyboard, a hardware button, a pointing device, a touch sensor, an illuminance sensor, an imaging device, an audio input device, an eye-gaze input device, an attitude sensing device, or the like can be used as the input unit 5240.

The display unit 5230 includes a display panel and has a function of displaying image data. For example, the display panel described in Embodiment 3 can be used for the display unit 5230.

The sensor unit 5250 has a function of supplying sensing data. For example, the sensor unit 5250 has a function of sensing a surrounding environment where the electronic device is used and supplying the sensing data.

Specifically, an illuminance sensor, an imaging device, an attitude sensing device, a pressure sensor, a human motion sensor, or the like can be used as the sensor unit 5250.

The communication unit 5290 has a function of receiving and supplying communication data. For example, the communication unit 5290 has a function of being connected to another electronic device or a communication network by wireless communication or wired communication. Specifically, the communication unit 5290 has a function of wireless local area network communication, telephone communication, near field communication, or the like.

FIG. 11B illustrates an electronic device having an outer shape along a cylindrical column or the like. An example of such an electronic device is digital signage. The display panel of one embodiment of the present invention can be used for the display unit 5230. The electronic device may have a function of changing its display method in accordance with the illuminance of a usage environment. The electronic device has a function of changing the displayed content when sensing the existence of a person. Thus, for example, the electronic device can be provided on a column of a building. The electronic device can display advertising, guidance, or the like.

FIG. 11C illustrates an electronic device having a function of generating image data on the basis of the path of a pointer used by the user. Examples of such an electronic device include an electronic blackboard, an electronic bulletin board, and digital signage. Specifically, a display panel with a diagonal size of 20 inches or longer, preferably 40 inches or longer, further preferably 55 inches or longer can be used. A plurality of display panels can be arranged and used as one display region. Alternatively, a plurality of display panels can be arranged and used as a multiscreen.

FIG. 11D illustrates an electronic device that is capable of receiving data from another device and displaying the data on the display unit 5230. An example of such an electronic device is a wearable electronic device. Specifically, the electronic device can display several options, and the user can choose some from the options and send a reply to the data transmitter. As another example, the electronic device has a function of changing its display method in accordance with the illuminance of a usage environment. Thus, for example, power consumption of the wearable electronic device can be reduced. As another example, the wearable electronic device can display an image so as to be suitably used even in an environment under strong external light, e.g., outdoors in fine weather.

FIG. 11E illustrates an electronic device including the display unit 5230 having a surface gently curved along a side surface of a housing. An example of such an electronic device is a mobile phone. The display unit 5230 includes a display panel that has a function of displaying images on the front surface, the side surfaces, the top surface, and the rear surface, for example. Thus, a mobile phone can display data on not only its front surface but also its side surfaces, top surface, and rear surface, for example.

FIG. 12A illustrates an electronic device that is capable of receiving data via the Internet and displaying the data on the display unit 5230. An example of such an electronic device is a smartphone. For example, the user can check a created message on the display unit 5230 and send the created message to another device. As another example, the electronic device has a function of changing its display method in accordance with the illuminance of a usage environment. Thus, power consumption of the smartphone can be reduced. As another example, it is possible to obtain a smartphone which can display an image such that the smartphone can be suitably used in an environment under strong external light, e.g., outdoors in fine weather.

FIG. 12B illustrates an electronic device that can use a remote controller as the input unit 5240. An example of such an electronic device is a television system. For example, data received from a broadcast station or via the Internet can be displayed on the display unit 5230. The electronic device can take an image of the user with the sensor unit 5250 and transmit the image of the user. The electronic device can acquire a viewing history of the user and provide it to a cloud service. The electronic device can acquire recommendation data from a cloud service and display the data on the display unit 5230. A program or a moving image can be displayed on the basis of the recommendation data. As another example, the electronic device has a function of changing its display method in accordance with the illuminance of a usage environment. Accordingly, for example, it is possible to obtain a television system which can display an image such that the television system can be suitably used even under strong external light entering the room from the outside in fine weather.

FIG. 12C illustrates an electronic device that is capable of receiving an educational material via the Internet and displaying it on the display unit 5230. An example of such an electronic device is a tablet computer. The user can input an assignment with the input unit 5240 and send it via the Internet. The user can obtain a corrected assignment or the evaluation from a cloud service and have it displayed on the display unit 5230. The user can select a suitable educational material on the basis of the evaluation and have it displayed.

For example, an image signal can be received from another electronic device and displayed on the display unit 5230. When the electronic device is placed on a stand or the like, the display unit 5230 can be used as a sub-display. Thus, for example, it is possible to obtain a tablet computer which can display an image such that the tablet computer is favorably used even in an environment under strong external light, e.g., outdoors in fine weather.

FIG. 12D illustrates an electronic device including a plurality of display units 5230. An example of such an electronic device is a digital camera. For example, the display unit 5230 can display an image that the sensor unit 5250 is capturing. A captured image can be displayed on the sensor unit. A captured image can be decorated using the input unit 5240. A message can be attached to a captured image. A captured image can be transmitted via the Internet. The electronic device has a function of changing shooting conditions in accordance with the illuminance of a usage environment. Accordingly, for example, it is possible to obtain a digital camera that can display a subject such that an image is favorably viewed even in an environment under strong external light, e.g., outdoors in fine weather.

FIG. 12E illustrates an electronic device in which the electronic device of this embodiment is used as a master to control another electronic device used as a slave. An example of such an electronic device is a portable personal computer. For example, part of image data can be displayed on the display unit 5230 and another part of the image data can be displayed on a display unit of another electronic device. Image signals can be supplied. Data written from an input unit of another electronic device can be obtained with the communication unit 5290. Thus, a large display region can be utilized in the case of using a portable personal computer, for example.

FIG. 13A illustrates an electronic device including the sensor unit 5250 that senses an acceleration or a direction. An example of such an electronic device is a goggles-type electronic device. The sensor unit 5250 can supply data on the position of the user or the direction in which the user faces. The electronic device can generate image data for the right eye and image data for the left eye in accordance with the position of the user or the direction in which the user faces. The display unit 5230 includes a display region for the right eye and a display region for the left eye. Thus, a virtual reality image that gives the user a sense of immersion can be displayed on the goggles-type electronic device, for example.

FIG. 13B illustrates an electronic device including an imaging device and the sensor unit 5250 that senses an acceleration or a direction. An example of such an electronic device is a glasses-type electronic device. The sensor unit 5250 can supply data on the position of the user or the direction in which the user faces. The electronic device can generate image data in accordance with the position of the user or the direction in which the user faces. Accordingly, the data can be shown together with a real-world scene, for example. Alternatively, an augmented reality image can be displayed on the glasses-type electronic device.

Note that this embodiment can be combined with any of the other embodiments in this specification as appropriate.

Embodiment 6

This embodiment will describe a structure in which any of the light-emitting devices described in Embodiment 2 is used as a lighting device with reference to FIGS. 14A and 14B. FIG. 14A illustrates a cross section taken along the line e-f in a top view of the lighting device in FIG. 14B.

In the lighting device in this embodiment, a first electrode 401 is formed over a substrate 400 that is a support and has a light-transmitting property. The first electrode 401 corresponds to the first electrode 101 in Embodiment 2. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a material having a light-transmitting property.

A pad 412 for applying voltage to a second electrode 404 is provided over the substrate 400.

An EL layer 403 is formed over the first electrode 401. The structure of the EL layer 403 corresponds to the structure of the EL layer 103 in Embodiment 2. Refer to the corresponding description for these structures.

The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 2. The second electrode 404 is formed using a material having high reflectance when light is extracted from the first electrode 401 side. The second electrode 404 is connected to the pad 412 so that voltage is applied to the second electrode 404.

As described above, the lighting device described in this embodiment includes a light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting device has high emission efficiency, the lighting device in this embodiment can have low power consumption.

The substrate 400 provided with the light-emitting device having the above structure and a sealing substrate 407 are fixed and sealed with sealing materials 405 and 406, whereby the lighting device is completed. It is possible to use only either the sealing material 405 or the sealing material 406. In addition, the inner sealing material 406 (not illustrated in FIG. 14B) can be mixed with a desiccant that enables moisture to be adsorbed, increasing the reliability.

When parts of the pad 412 and the first electrode 401 are extended to the outside of the sealing materials 405 and 406, the extended parts can serve as external input terminals. An IC chip 420 mounted with a converter or the like may be provided over the external input terminals.

Embodiment 7

This embodiment will describe application examples of lighting devices fabricated using the light-emitting apparatus of one embodiment of the present invention or the light-emitting device, which is part of the light-emitting apparatus with reference to FIG. 15 .

A ceiling light 8001 can be used as an indoor lighting device. Examples of the ceiling light 8001 include a direct-mount light and an embedded light. Such lighting devices are fabricated using the light-emitting apparatus and a housing and a cover in combination. Application to a cord pendant light (light that is suspended from a ceiling by a cord) is also possible.

A foot light 8002 lights a floor so that safety on the floor can be improved. For example, it can be effectively used in a bedroom, on a staircase, and on a passage. In such cases, the size and shape of the foot light can be changed in accordance with the dimensions and structure of a room. The foot light can be a stationary lighting device using the light-emitting apparatus and a support in combination.

A sheet-like lighting 8003 is a thin sheet-like lighting device. The sheet-like lighting, which is attached to a wall when used, is space-saving and thus can be used for a wide variety of uses. Furthermore, the area of the sheet-like lighting can be easily increased. The sheet-like lighting can also be used on an object such as a wall or a housing that has a curved surface.

A lighting device 8004 in which the direction of light from a light source is controlled to be only a desired direction can be used.

A desk lamp 8005 includes a light source 8006. As the light source 8006, the light-emitting apparatus of one embodiment of the present invention or the light-emitting device, which is part of the light-emitting apparatus, can be used.

Besides the above examples, when the light-emitting apparatus of one embodiment of the present invention or the light-emitting device, which is part of the light-emitting apparatus, is used as part of furniture in a room, a lighting device that functions as the furniture can be obtained.

As described above, a variety of lighting devices that include the light-emitting apparatus can be obtained. Note that these lighting devices are also embodiments of the present invention.

The structures described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

Embodiment 8

This embodiment will describe a light-emitting and light-receiving apparatus 810 with reference to FIGS. 16A to 16C, for description of a light-emitting device and a light-receiving device that can be used in a light-emitting apparatus of one embodiment of the present invention. The light-emitting and light-receiving apparatus 810 includes a light-emitting device and thus can be regarded as a light-emitting apparatus; includes a light-receiving device and thus can be regarded as a light-receiving apparatus; and can be used in a display unit in an electronic device and thus can be regarded as a display panel or a display device.

FIG. 16A is a schematic cross-sectional view of a light-emitting device 805 a and a light-receiving device 805 b included in the light-emitting and light-receiving apparatus 810 of one embodiment of the present invention.

The light-emitting device 805 a has a function of emitting light (hereinafter, also referred to as a light-emitting function). The light-emitting device 805 a includes an electrode 801 a, an EL layer 803 a, and an electrode 802. The light-emitting device 805 a is preferably a light-emitting device utilizing organic EL (an organic EL device) described in Embodiment 2. Thus, the EL layer 803 a interposed between the electrode 801 a and the electrode 802 includes at least a light-emitting layer. The light-emitting layer contains a light-emitting substance. The EL layer 803 a emits light when voltage is applied between the electrode 801 a and the electrode 802. The EL layer 803 a may include any of a variety of layers such as a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a carrier-blocking (hole-blocking or electron-blocking) layer, and a charge-generation layer, in addition to the light-emitting layer.

The light-receiving device 805 b has a function of sensing light (hereinafter, also referred to as a light-receiving function). As the light-receiving device 805 b, a PN photodiode or a PIN photodiode can be used, for example. The light-receiving device 805 b includes an electrode 801 b, a light-receiving layer 803 b, and the electrode 802. Thus, the light-receiving layer 803 b interposed between the electrode 801 b and the electrode 802 includes at least an active layer. Note that for the light-receiving layer 803 b, any of materials that are used for the variety of layers (e.g., the hole-injection layer, the hole-transport layer, the light-emitting layer, the electron-transport layer, the electron-injection layer, the carrier-blocking (hole-blocking or electron-blocking) layer, and the charge-generation layer) included in the above-described EL layer 803 a can be used. The light-receiving device 805 b functions as a photoelectric conversion device. When light is incident on the light-receiving layer 803 b, electric charge can be generated and extracted as a current. At this time, voltage may be applied between the electrode 801 b and the electrode 802. The amount of generated electric charge depends on the amount of the light incident on the light-receiving layer 803 b.

The light-receiving device 805 b has a function of sensing visible light. The light-receiving device 805 b has sensitivity to visible light. The light-receiving device 805 b further preferably has a function of sensing visible light and infrared light. The light-receiving device 805 b preferably has sensitivity to visible light and infrared light.

In this specification and the like, a blue (B) wavelength region ranges from 400 nm to less than 490 nm, and blue (B) light has at least one emission spectrum peak in the wavelength region. A green (G) wavelength region ranges from 490 nm to less than 580 nm, and green (G) light has at least one emission spectrum peak in the wavelength region. A red (R) wavelength region ranges from 580 nm to less than 700 nm, and red (R) light has at least one emission spectrum peak in the wavelength region. In this specification and the like, a visible wavelength region ranges from 400 nm to less than 700 nm, and visible light has at least one emission spectrum peak in the wavelength region. An infrared (IR) wavelength region ranges from 700 nm to less than 900 nm, and infrared (IR) light has at least one emission spectrum peak in the wavelength region.

The active layer in the light-receiving device 805 b includes a semiconductor. Examples of the semiconductor are inorganic semiconductors such as silicon and organic semiconductors such as organic compounds. As the light-receiving device 805 b, an organic semiconductor device (or an organic photodiode) including an organic semiconductor in the active layer is preferably used. An organic photodiode, which is easily made thin, lightweight, and large in area and has a high degree of freedom for shape and design, can be used in a variety of display devices. An organic semiconductor is preferably used, in which case the EL layer 803 a included in the light-emitting device 805 a and the light-receiving layer 803 b included in the light-receiving device 805 b can be formed by the same method (e.g., a vacuum evaporation method) with the same manufacturing apparatus. Note that any of the organic compounds of one embodiment of the present invention can be used for the light-receiving layer 803 b in the light-receiving device 805 b.

In the display device of one embodiment of the present invention, an organic EL device and an organic photodiode can be suitably used as the light-emitting device 805 a and the light-receiving device 805 b, respectively. The organic EL device and the organic photodiode can be formed over one substrate. Thus, the organic photodiode can be incorporated into the display device including the organic EL device. A display device of one embodiment of the present invention has one or both of an image capturing function and a sensing function in addition to a function of displaying an image.

The electrode 801 a and the electrode 801 b are provided on the same plane. In FIG. 16A, the electrodes 801 a and 801 b are provided over a substrate 800. The electrodes 801 a and 801 b can be formed by processing a conductive film formed over the substrate 800 into island shapes, for example. In other words, the electrodes 801 a and 801 b can be formed through the same process.

As the substrate 800, a substrate having heat resistance high enough to withstand the formation of the light-emitting device 805 a and the light-receiving device 805 b can be used. When an insulating substrate is used, a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, or the like can be used as the substrate 800. Alternatively, a semiconductor substrate can be used. For example, a single crystal semiconductor substrate or a polycrystalline semiconductor substrate of silicon, silicon carbide, or the like; a compound semiconductor substrate of silicon germanium or the like; an SOI substrate; or the like can be used.

In particular, it is preferable to use, as the substrate 800, the insulating substrate or the semiconductor substrate over which a semiconductor circuit including a semiconductor element such as a transistor is formed. The semiconductor circuit preferably constitutes part of a pixel circuit, a gate line driver circuit (a gate driver), a source line driver circuit (a source driver), or the like. In addition to the above, the semiconductor circuit may constitute part of an arithmetic circuit, a memory circuit, or the like.

The electrode 802 is formed of a layer shared by the light-emitting device 805 a and the light-receiving device 805 b. As the electrode through which light enters or exits, a conductive film that transmits visible light and infrared light is used. As the electrode through which light neither enters nor exits, a conductive film that reflects visible light and infrared light is preferably used.

The electrode 802 in the display device of one embodiment of the present invention functions as one of the electrodes in each of the light-emitting device 805 a and the light-receiving device 805 b.

In FIG. 16B, the electrode 801 a of the light-emitting device 805 a has a potential higher than the electrode 802. In this case, the electrode 801 a and the electrode 802 function as an anode and a cathode, respectively, in the light-emitting device 805 a. The electrode 801 b of the light-receiving device 805 b has a potential lower than the electrode 802. For easy understanding of the direction of current flow, FIG. 16B illustrates a circuit symbol of a light-emitting diode on the left of the light-emitting device 805 a and a circuit symbol of a photodiode on the right of the light-receiving device 805 b. The flow directions of carriers (electrons and holes) in each device are also schematically indicated by arrows.

In the structure illustrated in FIG. 16B, when a first potential is supplied to the electrode 801 a through a first wiring, a second potential is supplied to the electrode 802 through a second wiring, and a third potential is supplied to the electrode 801 b through a third wiring, the following relationship is satisfied: the first potential>the second potential>the third potential.

In FIG. 16C, the electrode 801 a of the light-emitting device 805 a has a potential lower than the electrode 802. In this case, the electrode 801 a and the electrode 802 function as a cathode and an anode, respectively, in the light-emitting device 805 a. The electrode 801 b of the light-receiving device 805 b has a potential lower than the potential of the electrode 802 and a potential higher than the potential of the electrode 801 a. For easy understanding of the direction of current flow, FIG. 16C illustrates a circuit symbol of a light-emitting diode on the left of the light-emitting device 805 a and a circuit symbol of a photodiode on the right of the light-receiving device 805 b. The flow directions of carriers (electrons and holes) in each device are also schematically indicated by arrows.

In the structure illustrated in FIG. 16C, when a first potential is supplied to the electrode 801 a through a first wiring, a second potential is supplied to the electrode 802 through a second wiring, and a third potential is supplied to the electrode 801 b through a third wiring, the following relationship is satisfied: the second potential>the third potential>the first potential.

FIG. 17A illustrates a light-emitting and light-receiving apparatus 810A that is a variation example of the light-emitting and light-receiving apparatus 810. The light-emitting and light-receiving apparatus 810A is different from the light-emitting and light-receiving apparatus 810 in including a common layer 806 and a common layer 807. In the light-emitting device 805 a, the common layers 806 and 807 function as part of the EL layer 803 a. In the light-receiving device 805 b, the common layers 806 and 807 function as part of the light-receiving layer 803 b. The common layer 806 includes a hole-injection layer and a hole-transport layer, for example. The common layer 807 includes an electron-transport layer and an electron-injection layer, for example.

With the common layers 806 and 807, a light-receiving device can be incorporated without a significant increase in the number of times of separate formation of devices, whereby the light-emitting and light-receiving apparatus 810A can be manufactured with a high throughput.

FIG. 17B illustrates a light-emitting and light-receiving apparatus 810B that is a variation example of the light-emitting and light-receiving apparatus 810. The light-emitting and light-receiving apparatus 810B is different from the light-emitting and light-receiving apparatus 810 in that the EL layer 803 a includes a layer 806 a and a layer 807 a and the light-receiving layer 803 b includes a layer 806 b and a layer 807 b. The layers 806 a and 806 b are formed using different materials, and each include a hole-injection layer and a hole-transport layer, for example. Note that the layers 806 a and 806 b may be formed using a common material. The layers 807 a and 807 b are formed using different materials, and each include an electron-transport layer and an electron-injection layer, for example. Note that the layers 807 a and 807 b may be formed using a common material.

An optimum material for forming the light-emitting device 805 a is selected for the layers 806 a and 807 a and an optimum material for forming the light-receiving device 805 b is selected for the layers 806 b and 807 b, whereby the light-emitting device 805 a and the light-receiving device 805 b can have higher performance in the light-emitting and light-receiving apparatus 810B.

The resolution of the light-receiving device 805 b described in this embodiment can be 100 ppi or higher, preferably 200 ppi or higher, further preferably 300 ppi or higher, still further preferably 400 ppi or higher, and still further preferably 500 ppi or higher, and 2000 ppi or lower, 1000 ppi or lower, or 600 ppi or lower, for example. In particular, when the resolution of the light-receiving device 805 b is 200 ppi or higher and 600 ppi or lower, preferably 300 ppi or higher and 600 ppi or lower, the display device of one embodiment of the present invention can be suitably applied to image capturing of fingerprints. In fingerprint authentication with the display device of one embodiment of the present invention, the increased resolution of the light-receiving device 805 b enables, for example, high accuracy extraction of the minutiae of fingerprints; thus, the accuracy of the fingerprint authentication can be increased. The resolution is preferably 500 ppi or higher, in which case the authentication conforms to the standard by the National Institute of Standards and Technology (NIST) or the like. On the assumption that the resolution of the light-receiving device is 500 ppi, the size of each pixel is 50.8 μm, which is adequate for image capturing of a fingerprint ridge distance (typically, greater than or equal to 300 μm and less than or equal to 500 μm).

The structures described in this embodiment can be used in appropriate combination with any of the structures described in the other embodiments.

Example 1 Synthesis Example 1

In this example, a method of synthesizing 8-(1,1′-biphenyl-4-yl)-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4PCDBfBfpm), which is the organic compound (Structural Formula (100)) described in Embodiment 1, is specifically described.

Step 1: Synthesis of 3-(9-chloro-2-dibenzofuranyl)-9-phenyl-9H-carbazole

Into a 2-L flask were put 30 g (110 mmol) of 8-bromo-1-chlorodibenzo[b,d]furan, 38 g (130 mmol) of 9-phenyl-9H-carbazole-3-boronic acid, 2.5 g (8.2 mmol) of tris(2-methylphenyl)phosphine (abbreviation: P(o-tolyl)₃), 40 g (290 mmol) of potassium carbonate (K₂CO₃), 550 mL of toluene, 80 mL of ethanol, and 80 mL of water. Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. The mixture was heated to 70° C. under a nitrogen stream, 720 mg (3.2 mmol) of palladium acetate (abbreviation: Pd(OAc)₂) was added thereto; then, the temperature of the mixture was raised to 90° C. and the mixture was stirred for 6 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with ethanol, so that 46 g of a white solid was obtained in a yield of 96%. A synthesis scheme of Step 1 is shown in (A-1) below.

Step 2: Synthesis of 9-phenyl-3-[9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-dibenzofuran-2-yl]-9H-carbazole

Into a 500 mL three-neck flask were put 14 g (32 mmol) of 3-(9-chloro-2-dibenzofuranyl)-9-phenyl-9H-carbazole obtained in Step 1, 14 g (55 mmol) of bis(pinacolato)diboron, 1.1 g (2.3 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (abbreviation: XPos), 12 g (110 mmol) of potassium acetate abbreviation: KOAc), and 200 mL of N,N′-dimethylformamide (abbreviation: DMF). Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 70° C. under a nitrogen stream, 640 mg (1.1 mmol) of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(dba)₂) was added thereto; then, the temperature was raised to 100° C. and the mixture was stirred for 3.5 hours. After the reaction, water was added to the mixture, and extraction with ethyl acetate was performed. The obtained organic layer was washed with water and saturated brine, and dried with magnesium sulfate. The obtained filtrate was condensed, and purification by silica gel column chromatography (toluene:hexane=1:1) was performed. The fraction was concentrated and dried to give 8.1 g of a pale yellow solid in a yield of 48%. A synthesis scheme of Step 2 is shown in (A-2) below.

Step 3: Synthesis of 8-chloro-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine

Into a 500 mL three-neck flask were put 3.6 g (15 mmol) of 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine, 7.2 g (14 mmol) of 9-phenyl-3-[9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-dibenzofuran-2-yl]-9H-carbazole obtained in Step 2, 270 mg (0.90 mmol) of tris(2-methylphenyl)phosphine, 6.2 g (45 mmol) of potassium carbonate, 100 mL of toluene, 20 mL of ethanol, and 20 mL of water. The mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 70° C. under a nitrogen stream, 100 mg (0.45 mmol) of palladium acetate was added thereto; then, the temperature was raised to 90° C. and the mixture was stirred for 2.5 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated to give 3.8 g of a yellow solid in a yield of 42%. A synthesis scheme of Step 3 is shown in (A-3) below.

Step 4: Synthesis of 8BP-4PCDBfBfpm

Into a 200 mL three-neck flask were put 1.9 g (3.0 mmol) of 8-chloro-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine obtained in Step 3, 1.0 g (5.1 mmol) of 4-biphenylboronic acid, 70 mg (0.20 mmol) of di(1-adamantyl)-n-butylphosphine (abbreviation: cataCXium (registered trademark) A), 0.69 g (4.52 mmol) of cesium fluoride (abbreviation: CsF), 2.0 g (6.0 mmol) of cesium carbonate (Cs₂CO₃), and 120 mL of diethylene glycol dimethyl ether (abbreviation: Diglyme). Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 70° C. under a nitrogen stream, 20 mg (90 μmol) of palladium acetate was added thereto; then, the temperature was raised to 130° C. and the mixture was stirred for 6.5 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with toluene to give 1.6 g of a pale yellow solid in a yield of 42%. Step 4 described above was again performed, whereby 2.4 g in total of a pale yellow solid was obtained. A synthesis scheme of Step 4 is shown in (A-4) below

<Purification by Sublimation>

With a train sublimation method, 2.3 g of the obtained pale yellow solid was purified by heating at 355° C. for 13 hours under a pressure of 2.92 Pa with an argon flow rate of 15 mL/min to give 1.5 g of a pale yellow solid at a collection rate of 71%. As the result of mass spectrometry analysis, the target 8BP-4PCDBfBfpm (mass number of 730) was found to be obtained.

FIGS. 18A and 18B show a nuclear magnetic resonance spectroscopy (¹H-NMR) chart of 8BP-4PCDBfBfpm after purification by sublimation in a deuterated chloroform (abbreviation: CDCl₃) solution. Note that the range of 6 from 0 to 10 ppm is shown in FIG. 18A and an enlarged view of the range of 6 from 6.9 to 9.7 ppm is shown in FIG. 18B. The results reveal that 8BP-4PCDBfBfpm was obtained.

¹H NMR (CDCl₃, 500 MHz): δ=7.11-7.14 (t, 1H), 7.32-7.60 (m, 12H), 7.69-7.86 (m, 11H), 7.91 (d, 1H), 8.01-8.08 (m, 4H), 8.66 (s, 1H), 9.50 (s, 1H).

<Measurement of Emission and Absorption Spectra>

The absorption spectrum and emission spectrum of 8BP-4PCDBfBfpm were measured. The absorption spectrum was measured with a UV-visible spectrophotometer (U-4100 manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured with a fluorescence spectrophotometer (FP-8600, manufactured by JASCO Corporation).

FIG. 19 shows the absorption spectrum and emission spectrum of a dichloromethane solution of 8BP-4PCDBfBfpm. The absorption spectrum of the solution was obtained by subtraction of a measured absorption spectrum of a solvent (dichloromethane) alone in a quartz cell from a measured absorption spectrum of the dichloromethane solution of 8BP-4PCDBfBfpm in a quartz cell.

FIG. 20 shows an absorption spectrum and an emission spectrum of a thin film. The solid thin film was formed over a quartz substrate by a vacuum evaporation method and another quartz substrate as the counter substrate was used to perform sealing; thus, a measurement sample was fabricated. Note that the emission spectrum was obtained by measurement of the measurement sample sealed, and the absorption spectrum was obtained by measurement of the sample from which the sealing was removed and the counter substrate was detached. The absorption spectrum of the thin film was obtained by subtraction of an absorption spectrum of a quartz substrate from an absorption spectrum of a 8BP-4PCDBfBfpm film formed over a quartz substrate. Even after the removal of the sealing at room temperature, any apparent change in film quality was not observed from the fabricated thin film and the stable amorphous film was found to be maintained. This revealed that the organic compound of the present application was able to form a thin film with excellent stability and the organic device fabricated with the organic compound of the present application exhibited excellent stability.

As shown in FIG. 19 , in the case of 8BP-4PCDBfBfpm in the dichloromethane solution, absorption peaks were observed at around 248 nm, 285 nm, and 352 nm, and an emission peak was observed at around 559 nm (excitation wavelength: 365 nm). As shown in FIG. 20 , in the case of the thin film of 8BP-4PCDBfBfpm, absorption peaks were observed at around 251 nm, 290 nm, and 372 nm, and an emission wavelength peak was observed at 497 nm (excitation wavelength: 360 nm). These results indicated that 8BP-4PCDBfBfpm was able to be effectively used as a light-emitting substance or a host material used in combination with a substance that emits light in the visible region. The results also indicated that 8BP-4PCDBfBfpm was able to be effectively used in a cap layer over a cathode.

<Tg Measurement>

The glass transition temperature (Tg) of 8BP-4PCDBfBfpm was measured. The Tg was measured with a differential scanning calorimeter (PYRIS 1 DSC manufactured by PerkinElmer Japan Co., Ltd.) in a state where a powder was put on an aluminum cell. The result showed that the Tg of 8BP-4PCDBfBfpm was 146° C. This reveals that the compound of the present invention exhibits significantly excellent thermal property and the thin film formed using such a compound is expected to have stable film quality. The use of the compound capable of forming a thin film with stable quality allows a highly heat-resistant organic device to be provided.

<Calculation of HOMO and LUMO Levels>

The HOMO level and the LUMO level of 8BP-4PCDBfBfpm were obtained through a cyclic voltammetry (CV) measurement. The calculation method is shown below.

An electrochemical analyzer (ALS model 600A or 600C, manufactured by BAS Inc.) was used as a measurement apparatus. To prepare a solution for the CV measurement, dehydrated dimethylformamide (DMF; produced by Sigma-Aldrich Inc., 99.8%, catalog No. 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (n-Bu₄NClO₄; produced by Tokyo Chemical Industry Co., Ltd., catalog No. T0836) as a supporting electrolyte was dissolved at a concentration of 100 mmol/L. Furthermore, the object to be measured was also dissolved at a concentration of 2 mmol/L.

A platinum electrode (PTE platinum electrode, manufactured by BAS Inc.) was used as a working electrode, another platinum electrode (Pt counter electrode for VC-3 (5 cm), manufactured by BAS Inc.) was used as an auxiliary electrode, and an Ag/Ag⁺ electrode (RE7 reference electrode for nonaqueous solvent, manufactured by BAS Inc.) was used as a reference electrode. Note that the measurement was performed at room temperature (20° C. to 25° C.).

In addition, the scan speed in the CV measurement was fixed to 0.1 V/sec, and an oxidation potential Ea [V] and a reduction potential Ec [V] with respect to the reference electrode were measured. The potential Ea is an intermediate potential of an oxidation-reduction wave, and the potential Ec is an intermediate potential of a reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this example with respect to the vacuum level is known to be −4.94 [eV], the HOMO level and the LUMO level can be calculated by the following formulae: HOMO level [eV]=−4.94−Ea and LUMO level [eV]=−4.94−Ec.

Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the hundredth cycle was compared with the oxidation-reduction wave in the first cycle to examine the electrical stability of the compound.

As a result, according to the measurement results of the oxidation potential Ea [V] of 8BP-4PCDBfBfpm, the HOMO level was found to be −5.80 eV. According to the measurement results of the reduction potential Ec [V], the LUMO level was found to be −3.04 eV.

The measurement result of the LUMO level indicated that 8BP-4PCDBfBfpm was probably able to transfer electrons suitably and able to be suitably used in an electron-transport layer, a light-emitting layer, and a charge generation layer of an organic device.

<Measurement of Refractive Index>

The refractive index of 8BP-4PCDBfBfpm was measured by a spectroscopic ellipsometer (M-2000U, produced by J.A. Woollam Japan Corp.). A 8BP-4PCDBfBfpm film used for the measurement was formed to a thickness of approximately 45 nm over a quartz substrate by a vacuum evaporation method. At a 633 nm wavelength, the ordinary refractive index n Ordinary (n_(o)) was 1.82. This revealed that 8BP-4PCDBfBfpm was also able to be effectively used as a material of a cap layer provided over a cathode in a light-emitting apparatus. As a material of the cap layer, the refractive index is preferably higher than or equal to 1.75 and lower than or equal to 2.50.

Example 2 Synthesis Example 2

In this example, a method of synthesizing 8-(1,1′-biphenyl-4-yl)-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mPCPDBfBfpm), which is the organic compound (Structural Formula (101)) described in Embodiment 1, is specifically described.

Step 1: Synthesis of 3-[3-(9-chloro-2-dibenzofuranyl)phenyl]-9-phenyl-9H-carbazole

Into a 500 mL flask were put 4.06 g (14.4 mmol) of 8-bromo-1-chlorodibenzo[b,d]furan, 6.29 g (17.3 mmol) of 3-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid, 5.38 g (38.9 mmol) of potassium carbonate (abbreviation: K₂CO₃), 80 mL of toluene, 11 mL of ethanol, and 11 mL of water. Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. The mixture was heated at 70° C. under a nitrogen stream, 395 mg (1.30 mmol) of tris(2-methylphenyl)phosphine (abbreviation: P(o-tolyl)₃) and 97 mg (0.43 mmol) of palladium acetate were added thereto; then, the temperature of the mixture was raised to 90° C. and the mixture was stirred for 6 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with ethanol, so that 6.84 g of a white solid was obtained in a yield of 91.2%. A synthesis scheme of Step 1 is shown in (B-1) below.

Step 2: Synthesis of 9-phenyl-3-[3-[9-(4,4,5,5-trimethyl-1,3,2-dioxaborolan-2-yl)-2-dibenzofuranyl]phenyl]-9H-carbazole

Into a 200 mL three-neck flask were put 6.80 g (13.1 mmol) of 3-[3-(9-chloro-2-dibenzofuranyl)phenyl]-9-phenyl-9H-carbazole obtained in Step 1, 5.00 g (19.7 mmol) of bis(pinacolato)diboron, 3.56 g (39.3 mmol) of potassium acetate (abbreviation: KOAc), and 65.5 mL of N,N-dimethylformamide (abbreviation: DMF). Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 50° C. under a nitrogen stream, 377 mg (0.79 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (abbreviation: XPhos) and 150 mg (0.26 mmol) of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(dba)₂) were added thereto; then, the temperature was raised to 100° C. and the mixture was stirred for 3.5 hours. After the reaction, water was added to the mixture, and extraction with ethyl acetate was performed. The obtained organic layer was washed with water and saturated brine, and dried with magnesium sulfate. The obtained filtrate was condensed, and purification by silica gel column chromatography (toluene:hexane=1:1) was performed. The fraction was concentrated and dried to give 4.44 g of a white yellow solid in a yield of 55.4%. A synthesis scheme of Step 2 is shown in (B-2) below.

Step 3: Synthesis of 8-chloro-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine

Into a 200 mL three-neck flask were put 1.42 g (5.95 mmol) of 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine, 4.00 g (6.54 mmol) of 9-phenyl-3-[3-[9-(4,4,5,5-trimethyl-1,3,2-dioxaborolan-2-yl)-2-dibenzofuranyl]phenyl]-9H-carbazole obtained in Step 2, 156 mg (0.38 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (abbreviation: SPhos), 2.65 g (19.2 mmol) of potassium carbonate, 32 mL of toluene, 11 mL of 1,4-dioxane, and 10 mL of water. Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 40° C. under a nitrogen stream, 42.7 mg (0.19 mmol) of palladium acetate was added thereto; then, the temperature was raised to 100° C. and the mixture was stirred for 3 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated to give 2.50 g of a light yellow solid in a yield of 61.1%. A synthesis scheme of Step 3 is shown in (B-3) below.

Step 4: Synthesis of 8BP-4mPCPDBfBfpm

Into a 200 mL three-neck flask were put 2.00 g (2.91 mmol) of 8-chloro-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine obtained in Step 3, 861 mg (4.35 mmol) of 4-biphenylboronic acid, 661 mg (4.35 mmol) of cesium fluoride (abbreviation: CsF), 1.89 g (5.80 mmol) of cesium carbonate (Cs₂CO₃), and 29 mL of diethylene glycol dimethyl ether (abbreviation: Diglyme). Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. The mixture was heated to 60° C. under a nitrogen stream, 62.4 mg (0.17 mmol) of di(1-adamantyl)-n-butylphosphine (abbreviation: cataCXium (registered trademark) A) and 19.5 mg (0.09 mmol) of palladium acetate were added thereto; then, the temperature of the mixture was raised to 130° C. and the mixture was stirred for 6.5 hours while being heated. 501 After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with toluene, so that 2.24 g of a pale yellow solid was obtained in a yield of 95.7%. A synthesis scheme of Step 1 is shown in (B-4) below.

<Purification by Sublimation>

With a train sublimation method, 2.23 g of the obtained pale yellow solid was purified by heating at 360° C. for 19 hours under a pressure of 3.11 Pa with an argon flow rate of 10 mL/min to give 1.66 g of a pale yellow solid at a collection rate of 74%. As the result of mass spectrometry analysis, the target 8BP-4mPCPDBfBfpm (mass number of 806) was found to be obtained.

FIGS. 21A and 21B show a nuclear magnetic resonance spectroscopy (¹H-NMR) chart of 8BP-4mPCPDBfBfpm after purification by sublimation in a deuterated chloroform (abbreviation: CDCl₃) solution. Note that the range of 6 from 0 to 10 ppm is shown in FIG. 21A and an enlarged view of the range of 6 from 7.1 to 9.7 ppm is shown in FIG. 21B. The results reveal that 8BP-4mPCPDBfBfpm was obtained.

¹H NMR (CDCl₃, 500 MHz): δ=7.32-7.50 (m, 10H), 7.56-7.74 (m, 15H), 7.80-7.86 (m, 3H), 7.95 (d, 1H), 8.08 (d, 1H), 8.20 (s, 1H), 8.30-8.34 (m, 2H), 8.56 (s, 1H), 9.53 (s, 1H).

<Measurement of Emission and Absorption Spectra>

The absorption spectrum and emission spectrum of 8BP-4PCDBfBfpm were measured as in Example 1. FIG. 22 shows the absorption spectrum and emission spectrum of a dichloromethane solution of 8BP-4PCDBfBfpm as in Example 1.

FIG. 23 shows an absorption spectrum and an emission spectrum of a thin film. Even after the removal of the sealing at room temperature, any apparent change in film quality was not observed from the fabricated thin film and the stable amorphous film was found to be maintained. This revealed that the organic compound of the present application was able to form a thin film with excellent stability and the organic device fabricated with the organic compound of the present application exhibited excellent stability.

As shown in FIG. 22 , in the case of 8BP-4mPCPDBfBfpm in the dichloromethane solution, absorption peaks were observed at around 246 nm, 285 nm, and 350 nm, and an emission peak was observed at around 572 nm (excitation wavelength: 370 nm). As shown in FIG. 23 , in the case of the thin film of 8BP-4mPCPDBfBfpm, absorption peaks were observed at around 248 nm, 284 nm, and 353 nm, and an emission wavelength peak was observed at 465 nm (excitation wavelength: 350 nm).

These results indicated that 8BP-4mPCPDBfBfpm was able to be effectively used as a light-emitting substance or a host material used in combination with a substance that emits light in the visible region. The results also indicated that 8BP-4mPCPDBfBfpm was able to be effectively used in a cap layer over a cathode.

<Tg Measurement>

The glass transition temperature (Tg) of 8BP-4mPCPDBfBfpm was measured as in Example 1 and found to be 148° C. This reveals that the compound of the present invention exhibits significantly excellent thermal property and the thin film formed using such a compound is expected to have stable film quality. The use of the compound capable of forming a thin film with stable quality allows a highly heat-resistant organic device to be provided.

<<Calculation of HOMO and LUMO>

The HOMO level and the LUMO level of 8BP-4mPCPDBfBfpm were calculated as in Example 1.

As a result, according to the measurement results of the oxidation potential Ea [V] of 8BP-4mPCPDBfBfpm, the HOMO level was found to be −5.80 eV. According to the measurement results of the reduction potential Ec [V], the LUMO level was found to be −3.04 eV.

The measurement result of the LUMO level indicated that 8BP-4mPCPDBfBfpm was probably able to transfer electrons suitably and able to be suitably used in an electron-transport layer, a light-emitting layer, and a charge generation layer of an organic device.

<Measurement of Refractive Index>

The refractive index of 8BP-4mPCPDBfBfpm was measured by a spectroscopic ellipsometer (M-2000U, produced by J.A. Woollam Japan Corp.). A 8BP-4mPCPDBfBfpm film used for the measurement was formed to a thickness of approximately 45 nm over a quartz substrate by a vacuum evaporation method. At a 633 nm wavelength, the ordinary refractive index n Ordinary (n₀) was 1.83. This revealed that 8BP-4mPCPDBfBfpm was also able to be effectively used as a material of a cap layer provided over a cathode in a light-emitting apparatus. As a material of the cap layer, the refractive index is preferably higher than or equal to 1.75 and lower than or equal to 2.50.

Example 3 Synthesis Example 3

In this example, a method of synthesizing 8-(1,1′:4′,1″-terphenyl-3-yl)-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4PCDBfBfpm), which is the organic compound (Structural Formula (102)) described in Embodiment 1, is specifically described.

Step 1: Synthesis of 8mpTP-4PCDBfBfpm

Into a 200 mL three-neck flask were put 1.9 g (3.10 mmol) of 8-chloro-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine obtained above in Step 3 of Synthesis Example 1, 1.7 g (4.7 mmol) of 2-[(1,1′:4′,1″-terphenyl)-3-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 67 mg (0.19 mmol) of di(1-adamantyl)-n-butylphosphine, 0.71 g (4.7 mmol) of cesium fluoride, 2.0 g (6.2 mmol) of cesium carbonate, and 40 mL of diethylene glycol dimethyl ether. Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. After that, the mixture was heated to 70° C. under a nitrogen stream, 21 mg (90 μmol) of palladium acetate was added thereto; then, the temperature was raised to 130° C. and the mixture was stirred for 6.5 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with toluene to give 1.4 g of a pale yellow solid in a yield of 56%. A synthesis scheme of Step 1 is shown in (C-1) below

<Purification by Sublimation>

With a train sublimation method, 1.4 g of the obtained pale yellow solid was purified by heating at 375° C. for 3.5 hours under a pressure of 2.79 Pa with an argon flow rate of 10 mL/min to give 1.1 g of a pale yellow solid at a collection rate of 80%. As the result of mass spectrometry analysis, the target 8mTP-4PCDBfBfpm (mass number of 805) was found to be obtained.

FIGS. 24A and 24B show a nuclear magnetic resonance spectroscopy (¹H-NMR) chart of 8mTP-4PCDBfBfpm after purification by sublimation in a deuterated chloroform (abbreviation: CDCl₃) solution. Note that the range of 6 from 0 to 10 ppm is shown in FIG. 24A and an enlarged view of the range of 6 from 7.0 to 9.8 ppm is shown in FIG. 24B. The results reveal that 8mTP-4PCDBfBfpm was obtained.

¹H NMR (CDCl₃, 500 MHz): δ=7.10-7.13 (t, 1H), 7.32-7.62 (m, 13H), 7.67 (d, 2H), 7.71-7.86 (m, 11H), 7.91 (d, 1H), 8.00-8.09 (m, 5H), 8.70 (s, 1H), 9.51 (s, 1H).

<<Measurement of Emission and Absorption Spectra>

The absorption spectrum and emission spectrum of 8mpTP-4PCDBfBfpm were measured as in Example 1. FIG. 25 shows the absorption spectrum and emission spectrum of a dichloromethane solution of 8mpTP-4PCDBfBfpm as in Example 1.

FIG. 26 shows an absorption spectrum and an emission spectrum of a thin film. Even after the removal of the sealing at room temperature, any apparent change in film quality was not observed from the fabricated thin film and the stable amorphous film was found to be maintained. This revealed that the organic compound of the present application was able to form a thin film with excellent stability and the organic device fabricated with the organic compound of the present application exhibited excellent stability.

As shown in FIG. 25 , in the case of 8mpTP-4PCDBfBfpm in the dichloromethane solution, absorption peaks were observed at around 253 nm, 280 nm, and 350 nm, and an emission peak was observed at around 550 nm (excitation wavelength: 380 nm). As shown in FIG. 26 , in the case of the thin film of 8mpTP-4PCDBfBfpm, absorption peaks were observed at around 253 nm, 285 nm, and 370 nm, and an emission wavelength peak was observed at 496 nm (excitation wavelength: 360 nm). These results indicated that 8mpTP-4PCDBfBfpm was able to be effectively used as a light-emitting substance or a host material used in combination with a substance that emits light in the visible region. The results also indicated that 8mpTP-4PCDBfBfpm was able to be effectively used in a cap layer over a cathode.

<Tg Measurement>

The glass transition temperature (Tg) of 8mpTP-4PCDBfBfpm was measured as in Example 1 and found to be 149° C. This reveals that the compound of the present invention exhibits significantly excellent thermal property and the thin film formed using such a compound is expected to have stable film quality. The use of the compound capable of forming a thin film with stable quality allows a highly heat-resistant organic device to be provided.

<Calculation of HOMO and LUMO>

The HOMO level and the LUMO level of 8mpTP-4PCDBfBfpm were measured as in Example 1 and found to be −5.80 eV and −3.04 eV, respectively.

The measurement result of the LUMO level indicated that 8mpTP-4PCDBfBfpm was probably able to transfer electrons suitably and able to be suitably used in an electron-transport layer, a light-emitting layer, and a charge generation layer of an organic device.

<Measurement of Refractive Index>

The n Ordinary (n_(o)) was found 1.83 from the measurement of the refractive index of 8mpTP-4PCDBfBfpm as in Example 1. This revealed that 8mpTP-4PCDBfBfpm was also able to be effectively used as a material of a cap layer provided over a cathode in a light-emitting apparatus.

Example 4 Synthesis Example 4

In this example, a method of synthesizing 8-(1,1′:4′,1″-terphenyl-3-yl)-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4mPCPDBfBfpm), which is the organic compound (Structural Formula (103)) described in Embodiment 1, is specifically described.

Step 1: Synthesis of 8mpTP-4mPCPDBfBfpm

Into a 200 mL three-neck flask were put 2.40 g (3.49 mmol) of 8-chloro-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine obtained above in Step 3 of Synthesis Example 2, 1.62 g (4.54 mmol) of 2-([1,1′:4′,1″-terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 796 mg (5.24 mmol) of cesium fluoride (abbreviation: CsF), 2.27 g (6.98 mmol) of cesium carbonate (Cs₂CO₃), and 18 mL of diethylene glycol dimethyl ether (abbreviation: Diglyme). Then, the mixture was degassed while the pressure in the flask was reduced, and the air in the flask was replaced with nitrogen. The mixture was heated to 60° C. under a nitrogen stream, 79.0 mg (0.22 mmol) of di(1-adamantyl)-n-butylphosphine (abbreviation: cataCXium (registered trademark) A) and 25.0 mg (0.11 mmol) of palladium acetate were added thereto; then, the temperature of the mixture was raised to 130° C. and the mixture was stirred for 6.5 hours while being heated. After the reaction, this mixture was suction-filtered, and the obtained residue was washed with water and ethanol. The resulting solid was dissolved in heated toluene, followed by suction filtration through a filter medium in which Celite, alumina, and Celite were stacked in this order. The obtained filtrate was concentrated and recrystallized with toluene, so that 2.70 g of a pale yellow solid was obtained in a yield of 87.7%. A synthesis scheme of Step 1 is shown in (D-1) below.

<Purification by Sublimation>

With a train sublimation method, 2.68 g of the obtained pale yellow solid was purified by heating at 380° C. for 18 hours under a pressure of 3.00 Pa with an argon flow rate of 10 mL/min to give 2.20 g of a pale yellow solid at a collection rate of 82%. As the result of mass spectrometry analysis, the target 8mpTP-4mPCPDBfBfpm (mass number of 882) was found to be obtained.

FIGS. 27A and 27B show a nuclear magnetic resonance spectroscopy (¹H-NMR) chart of 8mpTP-4mPCPDBfBfpm after purification by sublimation in a deuterated chloroform (abbreviation: CDCl₃) solution. Note that the range of 6 from 0 to 10 ppm is shown in FIG. 27A and an enlarged view of the range of 6 from 7.1 to 9.7 ppm is shown in FIG. 27B. The results reveal that 8mpTP-4mPCPDBfBfpm was obtained.

¹H NMR (CDCl₃, 500 MHz): δ=7.30-7.50 (m, 10H), 7.53-7.76 (m, 18H), 7.82-7.86 (m, 3H), 7.91 (s, 1H), 7.99 (d, 1H), 8.10 (d, 1H), 8.24 (s, 1H), 8.30 (d, 1H), 8.35 (s, 1H), 8.61 (s, 1H), 9.53 (s, 1H).

<Measurement of Emission and Absorption Spectra>

The absorption spectrum and emission spectrum of 8mpTP-4mPCPDBfBfpm were measured as in Example 1. FIG. 28 shows the absorption spectrum and emission spectrum of a dichloromethane solution of 8mpTP-4mPCPDBfBfpm as in Example 1.

FIG. 29 shows an absorption spectrum and an emission spectrum of a thin film. Even after the removal of the sealing at room temperature, any apparent change in film quality was not observed from the fabricated thin film and the stable amorphous film was found to be maintained. This revealed that the organic compound of the present application was able to form a thin film with excellent stability and the organic device fabricated with the organic compound of the present application exhibited excellent stability.

As shown in FIG. 28 , in the case of 8mpTP-4mPCPDBfBfpm in the dichloromethane solution, absorption peaks were observed at around 253 nm, 280 nm, and 337 nm, and an emission peak was observed at around 537 nm (excitation wavelength: 370 nm). As shown in FIG. 29 , in the case of the thin film of 8mpTP-4mPCPDBfBfpm, absorption peaks were observed at around 252 nm, 278 nm, and 350 nm, and an emission wavelength peak was observed at 468 nm (excitation wavelength: 350 nm). These results indicated that 8mpTP-4mPCPDBfBfpm was able to be effectively used as a light-emitting substance or a host material used in combination with a substance that emits light in the visible region. The results also indicated that 8mpTP-4mPCPDBfBfpm was able to be effectively used in a cap layer over a cathode.

<Tg Measurement>

The glass transition temperature (Tg) of 8mpTP-4mPCPDBfBfpm was measured as in Example 1 and found to be 151° C. This reveals that the compound of the present invention exhibits significantly excellent thermal property and the thin film formed using such a compound is expected to have stable film quality. The use of the compound capable of forming a thin film with stable quality allows a highly heat-resistant organic device to be provided.

<Calculation of HOMO and LUMO>

The HOMO level and the LUMO level of 8mpTP-4mPCPDBfBfpm were measured as in Example 1 and found to be −5.80 eV and −3.05 eV, respectively.

The measurement result of the LUMO level indicated that 8mpTP-4mPCPDBfBfpm was probably able to transfer electrons suitably and able to be suitably used in an electron-transport layer, a light-emitting layer, and a charge generation layer of an organic device.

<Measurement of Refractive Index>

The n Ordinary (n_(o)) was found 1.83 from the measurement of the refractive index of 8mpTP-4mPCPDBfBfpm as in Example 1. This revealed that 8mpTP-4mPCPDBfBfpm was also able to be effectively used as a material of a cap layer provided over a cathode in a light-emitting apparatus.

Example 5

In this example, Light-emitting device 1 and Light-emitting device 2, each of which is one embodiment of the present invention described in the above embodiment, and Comparative light-emitting device 3 are described. Structural formulae of organic compounds used for Light-emitting devices 1 and 2 and Comparative light-emitting device 3 are shown below.

(Fabrication Method of Light-Emitting Device 1)

In Light-emitting device 1 described in this example, as illustrated in FIG. 30 , a hole-injection layer 911, a hole-transport layer 912, a light-emitting layer 913, an electron-transport layer 914, and an electron-injection layer 915 are stacked in this order over a first electrode 901 formed over a glass substrate 900, and a second electrode 902 is stacked over the electron-injection layer 915.

First, indium tin oxide containing silicon oxide (ITSO) was deposited over the glass substrate 900 by a sputtering method to form the first electrode 901. Note that the film thickness was 70 nm and the area of the electrode was 2 mm×2 mm.

Next, in pretreatment for forming the light-emitting device over the substrate, the surface of the substrate was washed with water, baking was performed at 200° C. for one hour, and then UV ozone treatment was performed for 370 seconds. After that, the substrate was transferred into a vacuum evaporation apparatus where the pressure was reduced to approximately 10⁻⁴ Pa, vacuum baking was performed at 170° C. for 30 minutes in a heating chamber of the vacuum evaporation apparatus, and then the substrate was cooled down for approximately 30 minutes.

Then, the substrate provided with the first electrode 901 was fixed to a substrate holder provided in the vacuum evaporation apparatus such that the surface on which the first electrode 901 was formed faced downward. Over the first electrode 901, by an evaporation method using resistance heating, N-(1,1′-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) and a fluorine-containing electron acceptor material with a molecular weight of 672 (OCHD-003) were deposited by co-evaporation to a thickness of 10 nm such that the weight ratio of PCBBiF to OCHD-003 was 1:0.03, whereby the hole-injection layer 911 was formed.

Next, PCBBiF was deposited over the hole-injection layer 911 to a thickness of nm, and then 4,4′-diphenyl-4″-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP) was deposited to a thickness of 10 nm, whereby the hole-transport layer 912 was formed.

Then, over the hole-transport layer 912, 8mpTP-4PCDBfBfpm (Structural Formula (102)), which is an organic compound of one embodiment of the present invention, 9-(2-naphthyl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (abbreviation: βNCCP), and [2-d3-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN²)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d₃)₂(mbfpypy-d₃)) were deposited by co-evaporation to a thickness of 40 nm at a weight ratio of 0.6:0.4:0.1 (=8mpTP-4PCDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)), whereby the light-emitting layer 913 was formed.

After that, over the light-emitting layer 913, 2-{3-[3′-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq) represented by Structural Formula (iv) was deposited by evaporation to a thickness of 15 nm, and then, 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen) was deposited by evaporation to a thickness of 20 nm, whereby the electron-transport layer 914 was formed.

After the formation of the electron-transport layer 914, lithium fluoride (LiF) was deposited by evaporation to a thickness of 1 nm to form the electron-injection layer 915, and then aluminum (Al) was deposited by evaporation to a thickness of 200 nm to form the second electrode 902, whereby Light-emitting device 1 of this example was fabricated.

(Fabrication Method of Light-Emitting Device 2)

Light-emitting device 2 has a structure in which 8mpTP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 1 is replaced with 8-(1,1′:4′,1″-terphenyl-3-yl)-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8mpTP-4mPCPDBfBfpm) (Structural Formula (103)), which is an organic compound of one embodiment of the present invention. Specifically, Light-emitting device 2 was fabricated in a manner similar to that for Light-emitting device 1 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 8mpTP-4mPCPDBfBfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.6:0.4:0.1 (=8mpTP-4mPCPDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Comparative Light-Emitting Device 3)

Comparative light-emitting device 3 has a structure in which 8mpTP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 1 is replaced with 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm) and the mixture ratio between the organic compounds in the light-emitting layer 913 is modified. Specifically, Comparative light-emitting device 3 was fabricated in a manner similar to that for Light-emitting device 1 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 4,8mDBtP2Bfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=4,8mD BtP2Bfpm: βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

The device structures of Light-emitting devices 1 and 2 and Comparative light-emitting device 3 are listed in the following table.

TABLE 1 Film Comparative thickness Light-emitting Light-emitting light-emitting (nm) device 1 device 2 device 3 Second electrode 200 Al Electron-injection layer 1 LiF Electron-transport layer 20 NBPhen 15 2mPCCzPDBq Light-emitting layer 40 8mpTP-4PCDBfBfpm: 8mpTP-4mPCPDBfBfpm: 4,8mDBtP2Bfpm: βNCCP:dopant* βNCCP:dopant* βNCCP:dopant* (0.6:0.4:0.1) (0.6:0.4:0.1) (0.5:0.5:0.1) Hole-transport layer 10 PCBBi1BP 40 PCBBiF Hole-injection layer 10 PCBBiF:OCHD-003 (1:0.03) First electrode 70 ITSO *dopant = Ir(5mppy-d₃)₂(mbfpypy-d₃)

Light-emitting devices 1 and 2 and Comparative light-emitting device 3 were sealed using a glass substrate in a glove box containing a nitrogen atmosphere so as not to be exposed to the air (a sealing material was applied to surround the device and UV treatment and heat treatment at 80° C. for 1 hour were performed at the time of sealing). Then, the initial characteristics of the light-emitting devices were measured.

FIG. 31 shows the luminance-current density characteristics of Light-emitting devices 1 and 2 and Comparative light-emitting device 3. FIG. 32 shows the current efficiency-luminance characteristics thereof. FIG. 33 shows the luminance-voltage characteristics thereof. FIG. 34 shows the current-voltage characteristics thereof. FIG. 35 shows the external quantum efficiency-luminance characteristics thereof. FIG. 36 shows the emission spectra thereof. Table 2 shows the main characteristics of the light-emitting devices at a luminance of approximately 1000 cd/m². Note that luminance, CIE chromaticity, and emission spectra were measured with a spectroradiometer (SR-UL1R manufactured by TOPCON TECHNOHOUSE CORPORATION). The external quantum efficiency was calculated from the luminance and the emission spectra measured with the spectroradiometer, on the assumption that the light-emitting devices had Lambertian light-distribution characteristics.

TABLE 2 Current Current External Voltage Current density Chromaticity Chromaticity efficiency quantum (V) (mA) (mA/cm²) x y (cd/A) efficiency (%) Light-emitting 2.9 0.046 1.15 0.381 0.600 92.9 24.5 device 1 Light-emitting 2.8 0.035 0.88 0.378 0.602 96.8 25.5 device 2 Comparative light- 2.9 0.039 0.96 0.378 0.602 98.6 25.9 emitting device 3

It was found from FIG. 31 to FIG. 36 that Light-emitting devices 1 and 2 and Comparative light-emitting device 3 that were light-emitting devices of one embodiment of the present invention had emission efficiency equivalent to that of Comparative light-emitting device 3.

FIG. 37 shows luminance changes over driving time when Light-emitting devices 1 and 2 and Comparative light-emitting device 3 are driven at a constant current of 2 mA (50 mA/cm²). As shown in FIG. 37 , Light-emitting device 1 and Light-emitting device 2 each had a longer lifetime than Comparative light-emitting device 2. This indicated that the light-emitting devices using 8mpTP-4PCDBfBfpm and 8mpTP-4mPCPDBfBfpm, which are the organic compounds of one embodiment of the present invention, were able to have a longer lifetime than the light-emitting device using 4,8mDBtP2Bfpm.

Example 6

In this example, Light-emitting device 4 and Light-emitting device 5, each of which is one embodiment of the present invention described in the above embodiment, and Comparative light-emitting device 6 are described. Structural formulae of organic compounds used for Light-emitting devices 4 and 5 and Comparative light-emitting device 6 are shown below.

(Fabrication Method of Light-Emitting Device 4)

Light-emitting device 4 described in this example was fabricated like Light-emitting device 1 described in Example 5. Specifically, Light-emitting device 4 includes the light-emitting layer 913 formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 8mpTP-4PCDBfBfpm (Structural Formula (102)), βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.6:0.4:0.1 (=8mpTP-4mPCPDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Light-Emitting Device 5)

Light-emitting device 5 has a structure in which 8mpTP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 4 is replaced with 8-(1,1′-biphenyl-4-yl)-4-[8-(9-phenyl-9H-carbazol-3-yl)-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4PCDBfBfpm) (Structural Formula (100)), which is an organic compound of one embodiment of the present invention. Specifically, Light-emitting device 5 was fabricated in a manner similar to that for Light-emitting device 4 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 8BP-4PCDBfBfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.6:0.4:0.1 (=8BP-4PCDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Comparative Light-Emitting Device 6)

Comparative light-emitting device 6 has a structure in which 8mpTP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 4 is replaced with 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm) and the mixture ratio between the organic compounds in the light-emitting layer 913 is modified. Specifically, Comparative light-emitting device 6 was fabricated in a manner similar to that for Light-emitting device 4 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 4,8mDBtP2Bfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=4,8mD BtP2Bfpm: βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

The device structures of Light-emitting devices 4 and 5 and Comparative light-emitting device 6 are listed in the following table.

TABLE 3 Film Comparative thickness Light-emitting Light-emitting light-emitting (nm) device 4 device 5 device 6 Second electrode 200 Al Electron-injection layer 1 LiF Electron-transport layer 20 NBPhen 15 2mPCCzPDBq Light-emitting layer 40 8mpTP-4PCDBfBfpm: 8BP-4PCDBfBfpm: 4,8mDBtP2Bfpm: βNCCP:dopant* βNCCP:dopant* βNCCP:dopant* (0.6:0.4:0.1) (0.6:0.4:0.1) (0.5:0.5:0.1) Hole-transport layer 10 PCBBi1BP 40 PCBBiF Hole-injection layer 10 PCBBiF:OCHD-003 (1:0.03) First electrode 70 ITSO *dopant = Ir(5mppy-d₃)₂(mbfpypy-d₃)

Light-emitting devices 4 and 5 and Comparative light-emitting device 6 were sealed using a glass substrate in a glove box containing a nitrogen atmosphere so as not to be exposed to the air (a sealing material was applied to surround the device and UV treatment and heat treatment at 80° C. for 1 hour were performed at the time of sealing). Then, the initial characteristics of the light-emitting devices were measured.

FIG. 38 shows the luminance-current density characteristics of Light-emitting devices 4 and 5 and Comparative light-emitting device 6. FIG. 39 shows the current efficiency-luminance characteristics thereof. FIG. 40 shows the luminance-voltage characteristics thereof. FIG. 41 shows the current-voltage characteristics thereof. FIG. 42 shows the external quantum efficiency-luminance characteristics thereof. FIG. 43 shows the emission spectra thereof. Table 4 shows the main characteristics of the light-emitting devices at a luminance of approximately 1000 cd/m². Note that luminance, CIE chromaticity, and emission spectra were measured with a spectroradiometer (SR-UL1R manufactured by TOPCON TECHNOHOUSE CORPORATION). The external quantum efficiency was calculated from the luminance and the emission spectra measured with the spectroradiometer, on the assumption that the light-emitting devices had Lambertian light-distribution characteristics.

TABLE 4 Current Current External Voltage Current density Chromaticity Chromaticity efficiency quantum (V) (mA) (mA/cm²) x y (cd/A) efficiency (%) Light-emitting 2.8 0.039 0.97 0.380 0.600 93.3 24.7 device 4 Light-emitting 2.7 0.037 0.91 0.379 0.601 97.2 25.6 device 5 Comparative light- 2.9 0.047 1.17 0.377 0.603 98.4 25.9 emitting device 6

It was found from FIG. 38 to FIG. 43 that Light-emitting devices 4 and 5 and Comparative light-emitting device 6 that were light-emitting devices of one embodiment of the present invention had emission efficiency equivalent to that of Comparative light-emitting device 6.

FIG. 44 shows luminance changes over driving time when Light-emitting devices 4 and 5 and Comparative light-emitting device 6 are driven at a constant current of 2 mA (50 mA/cm²). As shown in FIG. 44 , Light-emitting device 4 and Light-emitting device 5 each had a longer lifetime than Comparative light-emitting device 5. This indicated that the light-emitting devices using 8mpTP-4PCDBfBfpm and 8BP-4PCDBfBfpm, which are the organic compounds of one embodiment of the present invention, were able to have a longer lifetime than the light-emitting device using 4,8mDBtP2Bfpm.

Example 7

In this example, Light-emitting device 7 and Light-emitting device 8, each of which is one embodiment of the present invention described in the above embodiment, and Comparative light-emitting device 9 and Comparative light-emitting device 10 are described. Structural formulae of organic compounds used for Light-emitting devices 7 and 8 and Comparative light-emitting devices 9 and 10 are shown below.

(Fabrication Method of Light-Emitting Device 7)

Light-emitting device 7 described in this example has a structure in which the mixture ratio between the organic compounds in the light-emitting layer 913 of Light-emitting device 5 described in Example 6 is modified. Specifically, Light-emitting device 7 was fabricated in a manner similar to that for Light-emitting device 5 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 8BP-4PCDBfBfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=8BP-4PCDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Light-Emitting Device 8)

Light-emitting device 8 has a structure in which 8BP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 7 is replaced with 8-(1,1′-biphenyl-4-yl)-4-[8-[3-(9-phenyl-9H-carbazol-3-yl)phenyl]-1-dibenzofuranyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mPCPDBfBfpm) (Structural Formula (101)), which is an organic compound of one embodiment of the present invention. Specifically, Light-emitting device 8 was fabricated in a manner similar to that for Light-emitting device 7 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 8BP-4mPCPDBfBfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=8BP-4mPCPDBfBfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Comparative Light-Emitting Device 9)

Comparative light-emitting device 9 has a structure in which 8BP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 7 is replaced with 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm). Specifically, Comparative light-emitting device 9 was fabricated in a manner similar to that for Light-emitting device 7 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of 4,8mDBtP2Bfpm, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=4,8mD BtP2Bfpm:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

(Fabrication Method of Comparative Light-Emitting Device 10)

Comparative light-emitting device 10 has a structure in which 8BP-4PCDBfBfpm used in the light-emitting layer 913 of Light-emitting device 7 is replaced with 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn). Specifically, Comparative light-emitting device 10 was fabricated in a manner similar to that for Light-emitting device 7 except that the light-emitting layer 913 was formed to a thickness of 40 nm over the hole-transport layer 912 by co-evaporation of PCDBfTzn, βNCCP, and Ir(5mppy-d₃)₂(mbfpypy-d₃) at a weight ratio of 0.5:0.5:0.1 (=PCDBfTzn:βNCCP:Ir(5mppy-d₃)₂(mbfpypy-d₃)).

The device structures of Light-emitting devices 7 and 8 and Comparative light-emitting devices 9 and 10 are listed in the following table.

TABLE 5 Film Comparative Comparative thickness Light-emitting Light-emitting light-emitting light-emitting (nm) device 7 device 8 device 9 device 10 Second electrode 200 Al Electron-injection layer 1 LiF Electron-transport layer 20 NBPhen 15 2mPCCzPDBq Light-emitting layer 40 8BP-4PCDBfBfpm: 8BP-4mPCPDBfBfpm: 4,8mDBtP2Bfpm: PCDBfTzn: βNCCP:dopant* βNCCP:dopant* βNCCP:dopant* βNCCP:dopant* (0.5:0.5:0.1) (0.5:0.5:0.1) (0.5:0.5:0.1) (0.5:0.5:0.1) Hole-transport layer 10 PCBBi1BP 40 PCBBiF Hole-injection layer 10 PCBBiF:OCHD-003 (1:0.03) First electrode 70 ITSO *dopant = Ir(5mppy-d₃)₂(mbfpypy-d₃)

Light-emitting devices 7 and 8 and Comparative light-emitting devices 9 and 10 were sealed using a glass substrate in a glove box containing a nitrogen atmosphere so as not to be exposed to the air (a sealing material was applied to surround the device and UV treatment and heat treatment at 80° C. for 1 hour were performed at the time of sealing). Then, the initial characteristics of the light-emitting devices were measured.

FIG. 45 shows the luminance-current density characteristics of Light-emitting devices 7 and 8 and Comparative light-emitting devices 9 and 10. FIG. 46 shows the current efficiency-luminance characteristics thereof. FIG. 47 shows the luminance-voltage characteristics thereof. FIG. 48 shows the current-voltage characteristics thereof. FIG. 49 shows the external quantum efficiency-luminance characteristics thereof. FIG. 50 shows the emission spectra thereof. Table 6 shows the main characteristics of the light-emitting devices at a luminance of approximately 1000 cd/m². Note that luminance, CIE chromaticity, and emission spectra were measured with a spectroradiometer (SR-UL1R manufactured by TOPCON TECHNOHOUSE CORPORATION). The external quantum efficiency was calculated from the luminance and the emission spectra measured with the spectroradiometer, on the assumption that the light-emitting devices had Lambertian light-distribution characteristics.

TABLE 6 External Current Current quantum Voltage Current density Chromaticity Chromaticity efficiency efficiency (V) (mA) (mA/cm²) x y (cd/A) (%) Light-emitting device 7 2.8 0.045 1.12 0.357 0.618 103.7 26.9 Light-emitting device 8 2.8 0.034 0.85 0.354 0.621 103.8 26.9 Comparative light- 2.8 0.033 0.83 0.350 0.623 104.5 27.0 emitting device 9 Comparative light- 2.6 0.032 0.81 0.354 0.621 98.0 25.4 emitting device 10

FIGS. 45 to 50 and the above table show that the emission efficiency of each of Light-emitting devices 7 and 8 of one embodiment of the present invention are equivalent to that of Comparative light-emitting device 9 and higher than that of Comparative light-emitting device 10.

FIG. 51 shows luminance changes over driving time when Light-emitting devices 7 and 8 and Comparative light-emitting devices 9 and 10 are driven at a constant current of 2 mA (50 mA/cm²). As shown in FIG. 51 , Light-emitting devices 7 and 8 each had a longer lifetime than Comparative light-emitting devices 9 and 10. This indicated that the light-emitting devices using 8BP-4PCDBfBfpm and 8BP-4mPCPDBfBfpm, which are the organic compounds of one embodiment of the present invention, were able to have a longer lifetime than the light-emitting device using 4,8mDBtP2Bfpm and PCDBfTzn.

This application is based on Japanese Patent Application Serial No. 2021-212283 filed with Japan Patent Office on Dec. 27, 2021, the entire contents of which are hereby incorporated by reference. 

What is claimed is:
 1. An organic compound represented by General Formula (G1),

wherein any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom, wherein any one of the carbon atoms is bonded to a group represented by General Formula (r1), and each of the others of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, wherein each of Q and Z independently represents an oxygen atom or a sulfur atom, wherein any one of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein any one of R³⁵ to R³⁸ represents any one of a substituted or unsubstituted polycyclic aromatic hydrocarbon group having 10 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 2. The organic compound according to claim 1, wherein General Formula (G1) is represented by General Formula (G2):

wherein any one of the carbon atoms in X¹ to X⁴ is bonded to a group represented by General Formula (r2), and each of the others of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein any one of R³² to R³⁸ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³² to R³⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein * represents a bond in General Formula (G2).
 3. The organic compound according to claim 1, wherein Ar¹ is fused to an adjacent ring at a given site.
 4. The organic compound according to claim 1, wherein Ar¹ is represented by any one of General Formula (t1), General Formula (t2-1), General Formula (t2-2), General Formula (t3-1) to General Formula (t3-3), and General Formula (t4),

wherein any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of R⁶ to R²⁷ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein * represents a site of fusion to a ring adjacent to Ar¹.
 5. The organic compound according to claim 1, wherein X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom.
 6. A thin film comprising the organic compound according to claim
 1. 7. A light-emitting device comprising the organic compound according to claim
 1. 8. A light-emitting apparatus comprising: the light-emitting device according to claim 7; and a transistor or a substrate.
 9. An electronic device comprising: the light-emitting apparatus according to claim 8; and a sensor unit, an input unit, or a communication unit.
 10. A lighting device comprising: the light-emitting apparatus according to claim 8; and a housing.
 11. An organic compound represented by General Formula (G1′),

wherein any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom, wherein any one of the carbon atoms is bonded to a group represented by General Formula (r1), and each of the others of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, wherein when Ar¹ represents a benzene ring, the benzene ring comprises at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of Q and Z independently represents an oxygen atom or a sulfur atom, wherein any one of R³¹ to R³⁴ represents a bond to any one of X¹ to X⁴, another one of R³¹ to R³⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R³¹ to R³⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein each of R³⁵ to R³⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 12. The organic compound according to claim 11, wherein Ar¹ is fused to an adjacent ring at a given site.
 13. The organic compound according to claim 11, wherein Ar¹ is represented by any one of General Formula (t1), General Formula (t2-1), General Formula (t2-2), General Formula (t3-1) to General Formula (t3-3), and General Formula (t4),

wherein any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of R⁶ to R²⁷ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein * represents a site of fusion to a ring adjacent to Ar¹.
 14. The organic compound according to claim 11, wherein X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom.
 15. A thin film comprising the organic compound according to claim
 11. 16. A light-emitting device comprising the organic compound according to claim
 11. 17. A light-emitting apparatus comprising: the light-emitting device according to claim 16; and a transistor or a substrate.
 18. An electronic device comprising: the light-emitting apparatus according to claim 17; and a sensor unit, an input unit, or a communication unit.
 19. A lighting device comprising: the light-emitting apparatus according to claim 17; and a housing.
 20. An organic compound represented by General Formula (G4):

wherein any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom, wherein any one of the carbon atoms is bonded to a group represented by General Formula (r3), and each of the others of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, wherein when Ar¹ represents a benzene ring, the benzene ring comprises at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of Q and Z independently represents an oxygen atom or a sulfur atom, wherein each of R³² to R³⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein any one of R³⁵ to R³⁸ represents a bond, and each of the others of R³⁵ to R³⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms forming a skeleton, wherein n represents an integer greater than or equal to 0 and less than or equal to 3, wherein any one of R⁴¹ to R⁴⁸ represents a bond, and each of the others of R⁴¹ to R⁴⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein R⁴⁹ represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group, and wherein * represents a bond in General Formula (G4).
 21. The organic compound according to claim 20, wherein General Formula (G4) is represented by General Formula (G5):

wherein each of X² to X⁴ independently represents a carbon atom or a nitrogen atom, wherein each of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 22. The organic compound according to claim 20, wherein Ar¹ is fused to an adjacent ring at a given site.
 23. The organic compound according to claim 20, wherein Ar¹ is represented by any one of General Formula (t1), General Formula (t2-1), General Formula (t2-2), General Formula (t3-1) to General Formula (t3-3), and General Formula (t4),

wherein any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of R⁶ to R²⁷ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein * represents a site of fusion to a ring adjacent to Ar¹.
 24. The organic compound according to claim 20, wherein X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom.
 25. The organic compound according claim 20, wherein the General Formula (G4) is represented by any of Structural Formula (100) to Structural Formula (103),


26. The organic compound according to claim 21, wherein the General Formula (G5) is represented by General Formula (G6):

wherein each of R³⁵, R³⁶ and R³⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein each of R⁴¹ and R⁴³ to R⁴⁸ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 27. The organic compound according to claim 26, wherein General Formula (G6) is represented by General Formula (G7):

wherein Ar² represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein each of R¹, R², and R⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 28. The organic compound according to claim 27, wherein General Formula (G7) is represented by General Formula (G8):

wherein k represents an integer of 0 or 1, and wherein each of R⁵⁰ to R⁶⁶ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton.
 29. An organic compound represented by General Formula (G3)×

wherein any one of X¹ to X⁴ represents a nitrogen atom, another one of X¹ to X⁴ represents a carbon atom, and each of the others of X¹ to X⁴ independently represents a carbon atom or a nitrogen atom, wherein each of the carbon atoms is independently bonded to any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms forming a skeleton, wherein any of the substituents bonded to the carbon atom comprises at least a dibenzofuran ring or a dibenzothiophene ring, and a carbazole ring, wherein Ar¹ represents a substituted or unsubstituted aromatic hydrocarbon having 6 to 30 carbon atoms forming a ring, and is fused to an adjacent ring at a given site, wherein when Ar¹ represents a benzene ring, the benzene ring comprises at least any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein Q represents an oxygen atom or a sulfur atom.
 30. The organic compound according to claim 29, wherein Ar¹ is represented by any one of General Formula (t1), General Formula (t2-1), General Formula (t2-2), General Formula (t3-1) to General Formula (t3-3), and General Formula (t4),

wherein any one of R¹ to R⁴ represents any one of a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and each of the others of R¹ to R⁴ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, wherein each of R⁶ to R²⁷ independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms forming a skeleton, and a substituted or unsubstituted heteroaryl group having 2 to 21 carbon atoms forming a skeleton, and wherein * represents a site of fusion to a ring adjacent to Ar¹.
 31. The organic compound according to claim 29, wherein X² represents a nitrogen atom, X³ represents a carbon atom, and X⁴ represents a nitrogen atom. 